Blog
At Generations Tax and Wealth Management, we’re passionate about helping individuals, families, and business owners take control of their financial futures. This blog is where we share professional guidance on tax planning, wealth management, retirement strategies, and current financial trends.
Whether you're planning for retirement, looking to minimize your tax burden, or simply want to make smarter money decisions, you'll find clear, actionable insights here. Our goal is to simplify complex topics and keep you informed with practical advice that makes a difference.
Thank you for joining us—your financial confidence starts here.
Medicare Open Enrollment 2026: What Should You Review Before Choosing a 2027 Plan?
Medicare Open Enrollment runs from October 15 through December 7. Learn what to review for 2027, including premiums, prescriptions, provider networks, out-of-pocket costs, and how Medicare fits into your retirement plan.
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What Is Tax-Loss Harvesting and When Does It Make Sense?
Tax-loss harvesting can help offset investment gains and potentially reduce your tax bill. Learn how the strategy works, when it may make sense, and what investors should know about the wash-sale rule.
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How Can I Lower My Tax Bill Before the End of the Year?
There may still be time to lower your 2026 tax bill before year-end. Review strategies involving retirement contributions, HSAs, investments, charitable giving, business expenses, withholding, and more.
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Should I Do a Roth Conversion Before the End of the Year?
A Roth conversion can be a powerful year-end tax planning strategy, but it is not right for everyone. Learn when a conversion may make sense, what tax impacts to consider, and why timing matters before December 31.
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7 Year-End Tax Planning Moves to Consider Before December 31
Year-end tax planning can help you make smarter financial decisions before December 31. Explore seven strategies involving income, retirement accounts, investments, charitable giving, RMDs, and more.
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5 Free Financial Tools You Can Use Right Now
From Roth conversion planning and investment research to tax withholding and loan calculators, these free financial tools can help you better understand your money and explore important financial decisions.
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Hyde Park Tampa: Historic Charm, Modern Energy, and One of the City’s Most Iconic Neighborhoods
Hyde Park blends historic homes, walkable streets, Bayshore Boulevard, local dining, shopping, and modern energy. Discover what makes this Tampa neighborhood one of the city’s most distinctive places to live and explore.
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2026 Tax Extension Deadlines: What Happens If You Miss the Deadline?
If your 2025 tax return is on extension, important 2026 deadlines are approaching. Learn when extended returns are due, what happens if you miss the deadline, and what to do if you still owe taxes or need documents.
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Florida Homestead Exemption Explained: What Tampa Homeowners Should Know
Own a home in Tampa? Learn how Florida’s Homestead Exemption, Save Our Homes cap and portability can affect your property taxes—and why the seller’s current tax bill may not reflect what you’ll pay.
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What’s Next for Water Street Tampa? Inside the District’s Next Evolution
Water Street Tampa is entering its next phase with a new entertainment district, 3,500-seat music venue, hotel, retail, parking, green space, and new residences. Here’s what’s coming next to downtown Tampa.
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Retiring in Tampa Bay? 7 Financial Things to Know Before You Make the Move
Thinking about retiring in Tampa Bay? Learn how Florida taxes, property costs, insurance, healthcare, Social Security and retirement withdrawals can affect your plan before making the move.
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The Real Cost of Buying a Home in Tampa Bay: 7 Expenses to Plan for Beyond the Mortgage
Buying a home in Tampa Bay? Look beyond the mortgage. Property taxes, insurance, flood risk, HOA/CDD fees, maintenance and closing costs can all affect what a home really costs and how it fits your financial plan.
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Tampa Bay Rays New Stadium Update: What’s Going On With the Proposed Tampa Ballpark?
The Tampa Bay Rays are closer than ever to a new stadium in Tampa. Here’s the latest on the proposed $2.3 billion ballpark, its location, financing, timeline, surrounding development, and what still needs approval.
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What’s Happening in St. Pete in September 2026? 10 Events & Things to Do
September is packed with things to do in St. Pete, from Rays baseball and Rowdies matches to ArtWalk, live music, museum events, waterfront activities, and local markets. See what’s happening around St. Petersburg this month.
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Which Tampa Suburb Is Best for Retirees?
Where should you retire in Tampa Bay? Compare Sun City Center and Palm Harbor and learn what retirees should consider before choosing a Tampa-area community.
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What’s Happening in Tampa in September 2026? 8 Events to Put on Your Calendar
September is packed with things to do around Tampa, from Buccaneers football and Lightning hockey to major concerts, Halloween events, downtown festivals, and more. See what’s happening around Tampa this month.
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How Do I Find a Good Financial Planner in Tampa?
Looking for a financial planner in Tampa? Learn what to look for, what questions to ask, how advisor minimums work, and why comprehensive planning matters.
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Back to School in Tampa: What Families Should Know for the 2026–27 School Year
Back-to-school season is here in Tampa. From school calendars and family budgets to extracurricular costs, college planning, and 529 savings, here are a few things families may want to keep in mind for the 2026–27 school year.
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What Is the Difference Between a CPA and a Tax Planner?
A CPA and a tax planner aren't necessarily the same thing. Learn the key differences, what qualifications matter, and how to choose the right tax professional for your needs.
Read MoreHow Do I Find a Good Tax Planner?
Finding a good tax planner is about more than getting your return filed. Learn what to look for, what questions to ask and why year-round tax planning can matter.
Read MoreHow Much Money Do I Need to Work With a Financial Advisor?
Think you need hundreds of thousands of dollars to work with a financial advisor? Learn how advisor minimums work, when financial guidance may help, and why Generations has no minimum.
Read MoreIs a CPA Better Than a Financial Advisor?
Should you work with a CPA, a financial advisor, or both? Learn the key differences between these professionals and how coordinated tax and financial planning can help support your broader financial goals.
Read MoreSurviving Student Loans: A Real-World Guide to Paying Them Off Faster
Fed up with student debt? Discover real-world tactics—repayment plans, refinancing tips, and automation hacks—in “Surviving Student Loans” to pay off your debt faster.
Read MoreJune Financial Focus: Mid-Year Wealth Check-In with Generations
Our clients trust us to provide guidance that’s timely, actionable, and personalized. June is one of the best times to regroup, refocus, and plan with purpose.
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Smart Financial Steps to Take This Month
As the midpoint of the year approaches, May is an ideal time to reassess, recalibrate, and reinforce your financial strategies. It’s easy to let your financial plans drift during the busyness of spring, but taking a few deliberate...
Read MoreThe Psychology of Love and Money
Money can be a touchy subject, especially regarding our closest relationships. Whether we like it or not, finance plays an integral role in our partnerships, families, and friendships. So, how can we foster healthy attitudes and...
Read MoreRules and Regulation Changes That Could Impact Your Finances in 2024
In the ever-evolving financial landscape, staying informed about the latest changes and potential implications for your retirement savings is crucial. Shifts in retirement regulations define 2024, and we’re committed to keeping...
Read MoreThe Big Game Indicator and Other Unusual Economic Theories
It’s a fun time of year for football fans. The NFL playoffs are starting, and the Big Game is just around the corner. While football fans will tune in for the matchups, commercials, and Usher’s Big Game halftime show, you...
Read MoreMajor Tax Changes Looming: Are You Ready?
With the start of the new year, we wanted to discuss a topic that will likely garner attention throughout 2024: the potential sunsetting of the Tax Cuts and Jobs Act (TCJA) in 2025. Although some of the provisions within the TCJA are...
Read MoreWhat to Know When Your Child Turns 18
Your Child is Turning 18: Handling Healthcare, Academics, and Finances Together As your child blows out the candles on their 18th birthday, you may still see your baby girl or boy. But in the eyes of the law your child is considered a...
Read MoreRecap and 2024 Outlook: Key Events and What May Be in Store
As we get ready to turn the page on 2023 and welcome the new year with all its possibilities, we’d like to take some time to reflect on the year that was—the notable events, trends, and developments that defined our...
Read MoreTechnology Guide for Dementia Patients and Their Caregivers
If you or a loved one has been diagnosed with Alzheimer's disease or any other form of dementia, this can be an extremely challenging time. While promising new treatments are developing and research continues, a cure remains elusive....
Read More10 Financial Missteps to Avoid During a Divorce
Divorce is one of the most stressful life events. Even the most amicable splits can be complicated and emotionally draining. We likely all know couples who have gone through divorce, and it can be a trying time for everyone involved....
Read MorePreparing for the Tax Cuts and Jobs Act Sunset at the End of 2025
While we haven’t yet said goodbye to 2023, it’s not too early to begin thinking about any tax changes that may be on the horizon. The Tax Cuts and Jobs Act (TCJA) of 2017 was designed to overhaul the federal tax code by...
Read More10 Ideas for a Virtual Holiday Party
Many of us have adapted to a world with remote team members and back-to-back Zoom calls with customers spread across the country, which certainly has its benefits. Nevertheless, one drawback is the difficulty of getting together in...
Read MoreThe Impact of SECURE 2.0 in 2024 and Beyond
SECURE 2.0: Changes Going Into Effect in 2024 Passed in 2019, the SECURE Act was the most substantial retirement legislation in over a decade. It contained important changes designed to help investors save more and be better prepared...
Read MoreA Year-End Financial Checklist
Time to Think About Year-End Financial Strategies As we roll into fall and the fourth quarter, now is a good time to pause and reflect on proactive ways to set up your finances for 2024. Economically speaking, we are now in a much...
Read MoreAI's Role in Shaping Our Tomorrow: A Look Ahead
While artificial intelligence (AI) is making headlines today, the concept of "thinking machines" can be traced back to ancient philosophers and mathematicians. The phrase artificial intelligence was first used in the mid-20th century,...
Read MoreTop 10 Questions High Net Worth Individuals Ask About Social Security
Social Security, the program you may have spent a lifetime paying into, is designed to offer stability, supplemental income, and other valuable benefits that can play a role in your overall financial strategy after you retire. We've...
Read MoreUnderstanding the September Effect: What It Is and Why It Happens
If you ask the average investor which month is the most volatile for the stock market, they will probably say October. It's a reasonable answer, but it's incorrect. Despite October's reputation for market-defining events like the...
Read MoreDon't Get Hooked: A Guide to Recognizing and Avoiding Phishing
As financial professionals, we understand how vital it is to safeguard your personal and financial information. Unfortunately, in our increasingly digital world, cybersecurity risks, such as phishing attacks, have become a prevalent...
Read MoreMoney Tips for Parents Sending Children Off to College
You’ve done a great job teaching your children vital life lessons and instilling values that will last a lifetime. As summer ends and a new school year begins, one thing that shouldn’t be overlooked, especially for...
Read MoreAttention Parents and Grandparents of College-Bound Students: FAFSA Gets an Overhaul
Changes are coming to the complicated form that students must submit to qualify for college financial aid, known as the Free Application for Federal Student Aid (FAFSA).The Department of Education is calling it the “most...
Read MoreThe 6 Biggest Mistakes DIY Investors Make and How to Avoid Them
IntroductionOver the last several months, I have met with quite a few self-proclaimed do-it-yourself (DIY) investors who, after struggling with the markets in 2022, approached me asking for a second opinion. Interestingly, almost every...
Read MoreHow the SECURE 2.0 Act Changed 529 Plans
Changes to 529 plans in the SECURE 2.0 ActThe SECURE Act was initially passed by Congress at the end of 2019 and was intended to improve retirement savings opportunities. It was a big deal at the time and the most significant piece of...
Read MoreHealth Savings Accounts: Pros, Cons, and Retirement Considerations
What if your child needs braces? The cost may be as much as $6,000 for metal braces—more modern versions can run as much as $13,000. Your health insurance may cover only a portion of the cost. If you're well past the braces stage...
Read MoreTop 7 Most Common Estate Strategy Mistakes (and How to Avoid Them)
Getting your affairs in order and outlining what you want done with your estate after you’re gone is one of the greatest gifts you can leave your loved ones. However, not preparing for the transfer of your assets can lead to...
Read MoreNavigating the Costs of Senior Care: Tips for Preparing for Long-Term Care
Senior care costs can be overwhelming, particularly when long-term care is required due to illness or medical conditions. With the number of seniors in the U.S. expected to rise exponentially by 2030, it's crucial to be prepared for...
Read MoreTrying to Time a Recession?
Economies move in cycles – always have, always willThe Federal Reserve has been steadily increasing interest rates in an attempt to slow the rate of inflation. Its efforts are yielding some results, although inflation remains...
Read MoreWhat Factors Have the Greatest Impact on Your Credit Score?
Fun fact: You probably have dozens of credit scores out there, and each one might be a different number.You’re probably familiar with a credit score, why it’s essential, and what it’s used for, but do you know how...
Read MoreImportant Financial Considerations to Make When Remarrying Later in Life
Discussing personal finances is important for any couple preparing for marriage. However, this topic can be more complicated for those who remarry later in life.If you’re remarrying later in life, one of your goals should be to...
Read MoreTop Considerations to Help Adult Children Be Better Prepared As You Age
As we get older, it’s important that our adult children are prepared to manage any aging-related situations that may arise. This includes everything from having to make medical and financial decisions to determining assisted...
Read MoreTips for Raising Financially Literate Children
Every parent wants the best for their children and strives to prepare them to lead a happy, healthy, and successful life. But, despite understanding the importance of financial responsibility, only 28 percent of parents speak to their...
Read MoreTransitioning to Medicare from Private Health Insurance Plans
Transitioning from Private Health Insurance Plans to MedicareAs you approach retirement age, you may be anticipating transitioning from your private insurance to Medicare, which is a federal health insurance program that provides...
Read MoreWhere to Put Excess Cash
According to the Investment Company Institute, near the end of 2022, there was more than $4.7 trillion in cash sitting in U.S. money market funds.1,2While cash can play a role in a diversified portfolio, historically, cash has not kept...
Read MoreTechnology Guide for Seniors
By 2040, the U.S. Census Bureau estimates that 80 million people in the U.S. will be age 65 or older.1 Most of these senior adults will either want to—or need to—"age in place," living in their homes securely, independently...
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