If you’ve ever shopped for health insurance outside of employer coverage, you know how confusing it can be. The options are overwhelming, the fine print is unclear, and it’s hard to know if you’re overpaying—or if your plan will truly protect you when you need it.
But here’s what most people don’t realize: the wrong health insurance decision can cost you thousands in unexpected taxes.
That’s where we come in. At Waldman Insurance Agency, a division of Waldman Accounting, we help individuals, families, and business owners find the right health insurance while ensuring every decision fits your broader financial and tax strategy.
The tax problems we keep seeing
We obtained our insurance licenses to bridge a critical gap: insurance decisions made without considering tax implications often lead to:
- Surprise subsidy repayments – Clients who purchased Marketplace coverage with income estimates that didn’t match their actual earnings face thousands in repayments at tax time.
- Missed deduction opportunities – Self-employed individuals who don’t properly structure their health insurance miss significant tax deductions.
- S-Corp compliance issues – Business owners who don’t understand 2% shareholder rules pay unnecessary taxes on health premiums.
- HSA eligibility mistakes – Choosing the wrong plan type can disqualify you from valuable HSA contributions.
These aren’t theoretical problems. We see them every tax season. And that’s exactly why we became licensed insurance professionals.
Understand your health insurance coverage options
From Marketplace (ACA) plans to private insurance and supplemental coverage, there’s no shortage of choices. That’s why it helps to work with advisors who understand your full financial picture and can guide you through:
Plan comparisons
- Comparing deductibles, premiums, and total out-of-pocket costs
- Checking provider networks and prescription coverage
- Spotting potential coverage gaps
- Weighing each policy’s true value based on your needs and budget
Strategic tax considerations
- Accurate income projections for subsidy eligibility
- Deduction optimization for self-employed coverage
- HSA eligibility and contribution strategies
- Impact on your overall tax situation
A licensed insurance advisor will explain your options and provide side-by-side comparisons—so you can see how each plan stacks up on coverage, cost, and long-term fit.
Why choose Waldman Accounting for insurance
If Waldman Accounting has prepared your tax return, we already have most of the information we need to guide you through insurance choices. With your email permission, we’ll review your current policy in advance and prepare tailored recommendations—making your meeting more accurate, efficient, and focused on decisions.
We know your financial picture
Existing clients can skip lengthy applications and get accurate quotes faster. We can use the secure information we already maintain (with your permission) to streamline the process.
Tax implications are built into every recommendation
From premium deductions to HSA strategies, we ensure your insurance choices support your overall tax plan.
Transparency over sales pressure
We outline the pros, cons, costs, and tax implications of every option, enabling you to make highly informed insurance decisions.
Ongoing coordination
Renewals, life changes, and tax season—we handle it all with the same team that knows your complete financial picture.
Smooth handoff into tax season
If you enjoy working with us, it’s easy to roll into tax time—just update us on any life or income changes, and we’ll align your benefits with your tax plan.
Where we’re licensed
Waldman Insurance Agency is licensed in Florida and works with clients remotely across most of the United States. We can help you find coverage that fits your needs regardless of where you live, with two exceptions: California and New York, where state regulations currently prevent us from offering services.
Let us take the confusion out of health insurance
We’re licensed and experienced health insurance advisors who bring a tax-smart approach to every conversation. Our remote service makes it easy to get expert help from anywhere in the country.
Whether you’re reviewing your current plan or shopping for new coverage during open enrollment, we’ll help you make informed decisions with confidence.
Schedule a free consultation and let us help you find a plan that fits both your coverage and tax goals: info@waldmanaccounting.com
This post is for general information and isn’t tax, legal, or insurance advice. Individual results depend on specific circumstances and current law. Always consult with licensed professionals for your situation.