Bonita Springs & Naples, Florida

Tax Planning
Built for
Retirement.

A year-round CPA relationship — proactive planning every fall, professional tax preparation every spring — designed exclusively for retirees, whether you live here year-round or spend the season in Southwest Florida.

Schedule a Free Intro Call See how it works
20+
Years CPA Experience
CPA/PFS
Tax & Financial Planning
$749
All-Inclusive Annual Fee
The Retirement Tax Plan
Annual Tax Package
Everything you need. One flat fee.
$749
/ year — all inclusive
  • ✓Fall Tax Planning Meeting — review income, Roth opportunities & year-end strategy before December 31st
  • ✓Federal Tax Return — investment income, Social Security, itemized deductions, prepared by a CPA
  • ✓State Return(s) — Florida and your home state if applicable
  • ✓Year-Round CPA Access — questions, estimated taxes, life changes anytime
  • ✓Secure 7-Year Document Storage — your returns on file, always accessible
Get Started — Schedule a Free Call

For personal retirement returns only. Business filings quoted separately.

Is This Right for You?

Built for Retirees with Real Assets
and Real Tax Questions

If you've built a portfolio of $1 million or more, your tax situation in retirement is more complex than most people realize — and more full of opportunity than most CPAs take the time to find.

Whether you call Southwest Florida home year-round or arrive every October, Sentinel Tax is designed for your situation. You're managing investment distributions, Social Security income, required minimum distributions, and possibly a home in another state. The decisions you make — and when you make them — have a meaningful impact on what you keep.

We don't do bookkeeping or payroll. We do one thing well: help retirees pay less tax through proactive, year-round planning.

Investment Portfolio Income Social Security Required Minimum Distributions Itemized Deductions Florida Full-Time Residents Seasonal Snowbirds Multi-State Returns
🌴
Florida Year-Round
  • In-person or virtual meetings on your schedule
  • Florida domicile planning and documentation
  • Federal return plus any prior-state obligations
  • Easy access throughout the year
✈️
Seasonal Snowbird
  • Fall planning meeting in person while you're here
  • Spring return prep before you head north
  • Home state return — no second accountant needed
  • Virtual support all summer long
The Annual Process

Two Key Moments.
Year-Round Relationship.

Most CPAs only talk to you in March or April — too late to change anything. Our model is built around working with you before year-end, when you can still act.

September — November

Fall Tax Planning Meeting

Before the calendar closes, we meet together — in person at our Bonita Springs office or virtually from wherever you are — to review your income picture and identify every opportunity to reduce your tax bill before December 31st.

  • Review estimated income and projected tax liability
  • Identify Roth conversion opportunities in your current bracket
  • Time capital gains and losses strategically
  • Plan charitable giving — including QCDs from your IRA
  • Review estimated tax payments and avoid underpayment penalties
  • IRMAA planning to protect next year's Medicare premiums
February — April

Spring Tax Return Preparation

When your documents arrive, we take it from there. Your return is prepared by a CPA — not outsourced, not automated — with a full review to confirm everything from the fall plan was executed correctly.

  • Federal return: investment income, Social Security, all schedules
  • Itemized deductions reviewed and fully maximized
  • State return — Florida and your home state if applicable
  • E-file with direct deposit for any refund
  • Secure 7-year storage of your completed return
  • Set up next year's estimated tax payments
Why Proactive Planning Matters

Most Retirees Are Leaving
Real Money on the Table

A reactive CPA files your taxes accurately. A proactive one helps you pay significantly less — by identifying opportunities that disappear the moment the calendar turns.

🔄

Roth Conversion Windows

Early retirement — before Social Security and RMDs kick in — often creates a window to convert IRA funds to Roth at historically low rates. Miss the window and it's gone forever.

🏥

IRMAA & Medicare Premiums

A single year of higher income can trigger a Medicare surcharge costing thousands in extra premiums two years later. We plan around the thresholds before they become a problem.

📈

Capital Gains Timing

When you sell, how much, and in which tax year are all choices. Strategic sequencing can keep you in the 0% long-term capital gains bracket — but only with advance planning.

🎁

Qualified Charitable Distributions

If you're 70½ or older and charitably inclined, giving directly from your IRA can satisfy your RMD without increasing taxable income — a meaningful advantage most retirees miss.

📅

RMD Planning

Required Minimum Distributions add to your taxable income whether you need the money or not. We help you plan around them proactively before they push you into a higher bracket.

⚖️

Tax Bracket Management

Retirement gives you more control over income than most people realize. We help you fill your bracket intentionally — minimizing taxes across your lifetime, not just this year.

In-Person or Virtual — Your Choice

Southwest Florida
Is Our Home Base.

Whether you're here year-round or arrive every October, our office in Bonita Springs is minutes from Naples and easy to get to. We're happy to meet in person — or handle everything virtually if you prefer.

For seasonal residents, we time both the fall planning meeting and spring tax preparation around your calendar so everything gets done while you're still in the area. For full-time Florida residents, we're available on a flexible schedule throughout the year.

Either way, we handle your home state return if you have one — no need to manage two accountants across two states.

📍 Bonita Springs, FL 📍 Naples, FL 💻 Virtual — Anywhere

Your Year with Sentinel Tax

September — October
Fall Planning Window Opens
In-person at our Bonita Springs office or virtually — your call
Oct — Nov
Fall Tax Planning Meeting
Year-end strategy, Roth conversions, estimated taxes, IRMAA review
December 31
Year-End Deadline
Last day for Roth conversions, charitable gifts, tax-loss harvesting
Feb — April
Spring Tax Preparation
Federal and state returns prepared and filed — in person or virtually
Year-Round
Ongoing CPA Access
Questions, life changes, estimated payments — we're here whenever you need us
About Sentinel Tax
Christopher G. Ragain, CPA/PFS — Sentinel Tax
20+
Years as CPA

A CPA Who Has Spent 20 Years
Finding What Others Miss

I'm Christopher G. Ragain, a CPA and Personal Financial Specialist based in Bonita Springs. After spending two decades helping business owners build and protect what they've earned, I've shifted my focus to what I find most meaningful — helping retirees keep more of what they've worked a lifetime to accumulate.

Most retirees I meet are working with a CPA who does an accurate job of filing their taxes. Accurate is fine. But in retirement, there are planning decisions — made before December 31st — that can save thousands of dollars a year. Those decisions don't happen in April. They happen in the fall. That's what we're built for.

Sentinel Tax is deliberately focused. We don't do bookkeeping, payroll, or business returns. We work exclusively with retirees and pre-retirees who have meaningful assets and want a CPA who thinks ahead alongside them — not just behind them.

Our office is at 3301 Bonita Beach Rd. in Bonita Springs. We serve clients who live here full-time, seasonal residents from across the country, and anyone who wants a proactive CPA relationship they can count on year-round.

CPA PFS — Personal Financial Specialist 20+ Years Experience Bonita Springs, FL
Ready to Get Started?

A Free 20-Minute Call.
No Obligation. No Pressure.

We'll spend a few minutes getting to know your situation — your income sources, your goals, and whether our annual package is a good fit for you. In person or virtual, whatever works best.

Schedule Your Free Intro Call →

Already have a CPA? Many clients switch to us after realizing how much proactive planning they've been missing.