Chaperone Health Insurance Plus
Medicare Questions Answered by a Medicare Advisor Near You in Fort Lauderdale
Medicare has a lot of moving parts, and most people only learn the rules when a deadline is already close. I’m Roxroy Ashley, an independent licensed agent with HealthMarkets and the owner of Chaperone Health Insurance Plus, a Black-owned agency in Fort Lauderdale. I’ve spent 14 years in insurance and the last 8 focused on Medicare, and I built this Medicare section of my Knowledge Center to answer the Medicare questions my clients ask most, in plain language.
Each guide covers one decision or deadline, from enrollment timing and the forms you need when you’re working past 65, to comparing plan types and understanding what drives your costs. Guides are reviewed for accuracy and show the plan year they cover. When you’d like to talk through your own situation, book a free plan review and I’ll get back to you personally within 24 to 48 hours.
LEARN AT YOUR OWN PACE
Get a Free Quote From an Independent Broker With Medicare Explained Simply
These guides help you understand your options. When you’re ready for answers about your own coverage, I check:
- Your doctors and hospitals against each plan’s network, including HCA Florida, Memorial, and Baptist Health
- Your prescriptions and pharmacy against each drug list
- Your full-year cost, not only the premium
If anything is unclear, I call your doctor’s office to confirm it. Your quote is free, with no obligation to enroll. Get your free quote and I’ll do the research for you.
Hear how I help you choose a plan with confidence.
MORE THAN A FREE QUOTE
Why Choose Me to Explain Medicare
When you’re choosing where to learn about Medicare, and who to call when you’re ready, here’s what to look for, and what you can expect from me.
Education First, in Plain Language: These guides are written the way I explain things to clients. My goal is for you to understand your options, not just pick a plan name off a list.
Reviewed for Accuracy: Medicare rules and figures change every year. Each guide shows the plan year it covers, and I update guides when Medicare publishes new figures.
Your Doctors, Hospitals, and Prescriptions Checked First: Reading is the first step. When you’re ready for answers about your own coverage, I do the checking. Before I recommend any plan, I check your doctors, hospitals, and every prescription against its network and drug list, including your pharmacy. If something is unclear, I’ll call your doctor’s office myself.
Every Question Answered, at Your Pace: Medicare has a lot of moving parts, and most people spend less than an hour choosing a plan. I take as long as you need, explain each piece in plain language, and answer every question until it makes sense. There’s no pressure and no obligation to enroll.
The Plan That Costs Less for You: The lowest premium isn’t always the lowest cost. I calculate your full-year cost for every plan, including copays, drug costs, and your out-of-pocket maximum, based on your health needs, before you choose.
My Help Costs You Nothing Extra: Insurers pay my commission, and plan premiums are generally the same whether you enroll through me or directly, so you get personal guidance and ongoing support at no additional charge.
Both Paths, Side by Side: Medicare Advantage, Medigap, and Part D each work differently. I lay out every path that fits your situation and explain what you’d gain and give up with each, so you decide with the full picture.
I Handle the Paperwork: If you choose a plan, I complete the application with you, confirm your enrollment window, and follow it through to approval, so the process is as simple as a conversation.
Licensed and Verified: I’m licensed in 33 states, I complete AHIP’s annual Medicare certification, and I’m certified for the 2027 plan year. You can verify my license (Florida License #W323530, NPN #17946070) anytime through your state’s insurance department.
I Stay Your Agent After You Enroll: Work with me directly, in person, by phone, on Zoom, or at your home in Broward, Miami-Dade, or Palm Beach, and I reply within 24 to 48 hours. I review your coverage every Annual Enrollment Period and help with claims and billing in between.
You can read all 25 reasons we should work together on my Why Choose Me page.
Medicare 101: Start Here
If you’re new to Medicare, start with the basics. Original Medicare is Part A (hospital insurance) and Part B (medical insurance). Most people then choose between two paths for the rest of their coverage. They can keep Original Medicare and add a Medicare Supplement (Medigap) plan and a Part D drug plan, or they can choose a Medicare Advantage plan, which is a different way to receive Part A and Part B benefits and often includes drug coverage.
For understanding Medicare as a whole, my overview of your Medicare options walks through each path, my Medicare Advantage plans page and Medicare Supplement plans page cover each path, and my Medicare Part D page covers prescription drug coverage in detail. Medicare isn’t only for people turning 65. People under 65 may qualify because of a disability or certain medical conditions.
Medicare Open Enrollment and 2027 Changes
The Annual Enrollment Period runs October 15 to December 7, 2026, for coverage starting January 1, 2027. These guides help you review your current plan and understand what’s changing:
2027 Medicare Open Enrollment Checklist for Florida: what to review before December 7, including your doctors, prescriptions, and your plan’s Annual Notice of Change.
2027 Medicare Advantage Changes in South Florida: what’s changing for 2027 and how to check whether your plan is affected.
What Your 2027 Medicare ANOC or Non-Renewal Notice Means: how to read your Annual Notice of Change, and what to do if your plan is leaving your area.
Switching From Medicare Advantage to Medigap Without Underwriting: when a plan leaving South Florida may give you guaranteed issue rights to a Medigap plan.
How to Apply for Medicare, Turning 65, and Working Past 65
Enrollment timing is where costly mistakes happen most often. These guides walk through each step:
Turning 65 Medicare Checklist: what to do and when, before and after your 65th birthday.
How to Apply for Medicare Online, Starting With Login.gov: setting up your accounts and what you need before you apply.
CMS-L564 and CMS-40B: Medicare Forms for Working Past 65: the two forms used to sign up for Part B after employer coverage ends.
COBRA and Medicare at 65: why COBRA doesn’t protect your Part B timing the way active employer coverage does.
Medigap vs. Medicare Advantage and Other Plan Comparisons
Choosing between plan types is one of the biggest Medicare decisions, and the right answer depends on your doctors, your health, and how you like to get care:
Medicare Advantage vs. Medicare Supplement in Broward County: how the two paths compare on networks, costs, and travel.
Medicare Plan G vs. Plan N in Florida: two popular Medigap plans and how their cost sharing differs.
Medicare Advantage HMO vs. PPO in Broward County: networks, referrals, and out-of-network coverage.
Medicare Costs and IRMAA
What you pay for Medicare depends on more than your premium. These guides explain what drives your costs, without quoting plan premiums, since those depend on your age, location, and plan:
How Much Does Medicare Supplement Insurance Cost in Fort Lauderdale?: the factors that set Medigap premiums in Florida.
2027 Medicare Part D Costs: the 2027 deductible limit, drug cost stages, and out-of-pocket limit.
Medicare Planning for High-Net-Worth South Floridians: how IRMAA works, and how income decisions like Roth conversions can affect Medicare premiums.
Moving to Florida and Getting Ready for Your Plan Review
Moving to Florida With Medicare: what to review before and after a move, from plan availability to your doctors and pharmacy.
What to Bring to a Medicare Consultation in Fort Lauderdale: the documents and details that make your plan review faster and more accurate.
Browse the Knowledge Base
Enrollment and Timing
MORE WAYS I CAN HELP
Find the Right Coverage for Every Stage of Life
Most households need more than one kind of coverage, and what you need changes as life does. Keep reading for the details on this page, or see all the coverage I help with and my guides to each type of insurance:
Frequently Asked Medicare Questions and Answers
Where Should I Start if I’m New to Medicare?
Start with Medicare 101 above, then read the Turning 65 Medicare Checklist. If you’re still working past 65, the CMS-L564 and CMS-40B guide explains how to sign up for Part B when your employer coverage ends.
Are These Guides a Substitute for a Plan Review?
No. The guides explain how Medicare works in general. Your best plan depends on your doctors, prescriptions, location, and budget, so a free plan review is the best way to apply what you’ve read to your own situation.
Are These Guides Up to Date?
Each guide shows the plan year it covers and when it was last reviewed. Medicare figures, such as Part D limits and IRMAA brackets, change every year, and I update the guides when new figures are published.
Where Else Can I Get Medicare Information?
Medicare.gov and 1-800-MEDICARE (TTY users should call 1-877-486-2048), available 24 hours a day, 7 days a week, have information on all of your options. In Florida, you can also get free, unbiased Medicare counseling through the state’s SHIP program, called SHINE. You can also find short Medicare explainers on my TikTok.
Can I Use These Guides to Help a Parent With Medicare?
Yes. Many of my clients first reach out while helping a parent. The guides are a good place to start, and with your parent’s permission, I’m glad to include you in their plan review, by phone, on Zoom, or at their home in Broward, Miami-Dade, or Palm Beach.
Can You Help With Coverage Other Than Medicare?
Yes. I also help with ACA Marketplace plans for people under 65, small business group plans, and dental, vision, life, and supplemental insurance. Answers to general questions are on my FAQ page.
Book a Free Plan Review
Have a question these guides didn’t answer? Pick a time for a free 15-minute call by phone or video. I’ll check whether your doctors are covered, and my help never costs you anything extra.
Call or text: (954) 410-3710
Email: contact@chaperonehealthinsuranceplus.com
Office: 6360 NW 5th Way Ste 101, Fort Lauderdale, FL 33309
Meet by: phone, video, at my office, or at home in Broward, Miami-Dade and Palm Beach.
- How It Works
How we'll work together
Five steps, no pressure, and I stay with you after you enroll.
1
We talk about you
By phone, Zoom or face to face. Your health, your budget, your doctors.
2
I check the details
Doctors, hospitals, prescriptions and pharmacy, checked against each plan.
3
We compare real costs
A full-year estimate for each option, explained in plain language.
4
You decide, I enroll you
No pressure. If you choose a plan, I handle the application with you.
5
We review every year
Plans and networks change. I check yours each year and help with claims in between.