You're at a crossroads.

We know the way.

Whether you're approaching retirement, navigating a disability, a veteran, or managing benefits for your team — Senior Street Advisory provides honest, clear guidance. Find your situation below.

Who We Serve

Retirees & Pre-Retirees

You've worked hard your entire life. The last thing you should have to navigate is the most confusing benefits system in America — alone, on a deadline, with permanent consequences for getting it wrong.

Sound familiar?

"I'm turning 65 in three months. My inbox is full of Medicare mailers I don't understand, my HR department says I need to act, and every time I research online I get more confused. I don't want to make a mistake I can't undo."

What you're actually dealing with

Permanent penalties for missing enrollment deadlines
Medicare's Initial Enrollment Period is just 7 months. Miss it, and you face a 10% Part B penalty — every year, for the rest of your life. Part D drug penalties add another 1% per month with no cap.
The COBRA trap
Many people buy COBRA after leaving a job thinking they have time. What they don't know: COBRA does not pause your Medicare enrollment window. When COBRA ends, they can be left with gaps — and penalties.
Medicare Advantage vs. Supplement paralysis
Both options have real trade-offs. Advantage plans have lower premiums but narrow networks and out-of-pocket maximums up to $9,250. Supplements cost more monthly but protect you from large bills. The right answer depends on your health, doctors, and budget.
Drug coverage surprises when plans quietly change formularies each year
A medication that cost $30 last year can jump to $300+ when a plan quietly drops it from its formulary. Annual plan reviews aren't optional — they're essential.

How SSA Guides You

Enrollment timeline review
We identify your exact enrollment windows before they close — no penalties, no surprises.
Plain-English plan comparison
We compare Advantage vs. Supplement using your actual doctors, medications, and budget.
Annual drug plan audit
We review your Part D plan against your current prescriptions every fall before the enrollment window closes.
Employer-to-Medicare transition
We coordinate the timing of leaving group coverage so you never face a gap or a preventable penalty.
Enrollment handled alongside you
We walk through the process with you so nothing gets missed.

Who We Serve

Under 65 & Medicaid

Living with a disability or a limited income doesn't mean you should settle for less than the best coverage available to you. Navigating Medicaid and Medicare at the same time is complex — and the stakes are high.

Sound familiar?

"I'm on SSDI and was just told I'd automatically get Medicare in two years. I also have Medicaid. I don't understand how they work together, which one pays first, or whether I even need both. No one has explained this to me."

What you're actually dealing with

Income changes that can flip your coverage — sometimes overnight
A small raise, a part-time job, or a spouse's new hours can push you over the Medicaid threshold — triggering an involuntary plan switch mid-year, with your providers potentially changing overnight.
Dual eligibility confusion
When you qualify for both Medicare and Medicaid, knowing which program pays first — and for what — is genuinely complicated. Care coordination gaps between the two systems are common and costly.
Missing D-SNP benefits most people don't know they qualify for
Dual Special Needs Plans offer benefits many people never hear about — including meal delivery, transportation, and home modifications. If no one tells you, you won't know to ask.
Staying in a plan that isn't working because no one explained you can switch
Dual-eligible individuals can switch plans monthly under a Special Enrollment Period — but most don't know this and stay in plans that aren't serving them well.

How SSA Guides You

Income scenario planning
We show you exactly where Medicaid thresholds are and what coverage changes to expect before they happen.
Medicare + Medicaid coordination
We explain which program covers what, which pays first, and where the gaps are.
D-SNP benefit review
We identify whether you qualify for a Dual Special Needs Plan and which options offer the most value in your area.
Annual plan comparison
We review your plan each year and flag when a switch would unlock better benefits or lower costs.
Connection to local resources
We connect you to state Medicaid counselors and community support programs that extend your coverage further.

Who We Serve

Veterans

You served this country and earned your benefits. But VA coverage has real limits many veterans don't discover until it's too late — and the gap between what you think you're covered for and what the VA actually pays can be significant.

Sound familiar?

"I always assumed my VA benefits covered everything. Then I had an emergency while traveling and found out the VA doesn't pay for non-VA facilities. Now I'm 66, past my Medicare enrollment window, and facing penalties I didn't know were coming."

What you're actually dealing with

Assuming VA coverage is comprehensive when it isn't
VA benefits do not cover everything. Non-service-connected conditions — arthritis, high cholesterol, diabetes in many cases — may require Medicare or private coverage. Veterans who assume they're fully covered often discover otherwise at the worst possible moment.
VA network restrictions
The VA only covers care at VA facilities or VA-authorized providers. A medical emergency while traveling, or a specialist your VA doesn't offer, can result in bills the VA won't pay. Medicare provides nationwide coverage the VA simply cannot match.
Missing Medicare enrollment windows because VA coverage felt like enough
Veterans who rely solely on VA benefits often miss their Medicare Initial Enrollment Period at 65, not realizing VA coverage doesn't satisfy the Medicare enrollment requirement. The result: permanent Part B penalties.

How SSA Guides You

VA benefits review
We walk through what your VA benefits do and don't cover so there are no surprises when care is needed.
Medicare enrollment review
We confirm your enrollment status before age 65 to ensure you enroll on time and avoid lifetime penalties.
VA + Medicare coordination
We explain how your VA benefits and Medicare work together and where a supplement plan fills the remaining gaps.

Who We Serve

Business Owners & HR Managers

Benefits decisions affect your bottom line and your team's wellbeing. The rules are complex, they change frequently, and the cost of getting them wrong falls on you.

Sound familiar?

"One of my longest employees just turned 65. I thought they were covered under our group plan. My accountant told me that since we have fewer than 20 employees, Medicare should have been their primary coverage — and we may have been billing payroll deductions incorrectly."

What you're actually dealing with

The age-65 Medicare primary rule
For businesses with fewer than 20 employees, Medicare becomes the primary payer the moment an employee turns 65 — whether they enroll or not. Continuing to bill group plan premiums without coordinating Medicare is a compliance exposure most small employers don't know about.
No clear process for guiding employees through Medicare enrollment
When employees approach 65, most HR managers have no playbook for guiding them through Medicare enrollment alongside group coverage. The result: confused employees, delayed enrollments, and preventable penalties.
Owner coverage gaps
As a business owner, your individual health insurance options are more expensive and less subsidized than a W-2 employee's — and planning ahead is critical to managing premium costs effectively.

How SSA Guides You

Benefits compliance review
We review your current group plan setup and flag any age-65 Medicare coordination issues before they become a liability.
Employee Medicare transition support
We build a simple "Age 65 Playbook" your HR team can use to guide employees through enrollment at the right time, every time.
Owner coverage planning
We review your personal health and life insurance options as a business owner, including key person coverage.
Ongoing advisory relationship
As your team grows and ages, we're available to review benefit decisions and keep you on track.

Not sure which category fits you?

That's exactly what we're here for. Tell us your situation and we'll help you figure out where you stand — and what to do next. No obligation, no pressure.