Steven DiPaolo, Medicare Insurance Broker

About Me

Hi, I’m Steven DiPaolo, a dedicated Medicare broker and advisor committed to helping you navigate the complexities of Medicare with confidence.

My approach is simple: I build genuine, lasting relationships to understand what matters most to you, ensuring you get a plan tailored to your unique needs.

With my expertise, I guide you through comparing top-rated Medicare plans from national and local providers, analyzing potential costs for treatments and medications, and developing a personalized strategy to maximize your benefits while minimizing expenses.

Did you know? Brokers like me are paid by insurance companies, so my services come at no cost to you.

Choosing to "DIY" your Medicare coverage can mean missing out on valuable benefits or savings. Working with a licensed professional ensures you get the best options available. My advice? Don’t just shop for plans—shop for the right broker. Not all brokers are the same, and finding someone whose approach and personality align with your needs makes all the difference.

What sets me apart is my commitment to exceptional customer service. I treat every client like a friend, not just a transaction, and I’m confident that my dedication and expertise will earn your trust. Let’s work together to secure the Medicare plan that’s right for you—today and for years to come.

Contact me now to explore your Medicare options! Mention that you found me on Medicare Agents Hub, and let’s start building a plan—and a friendship—that lasts.

Get in touch with Steven using this form

Q&A with Steven DiPaolo

Answer: No, but you may want to check it out.

New York rates are very high, and you may be able to get a better rate in FL for the same plan.

Answer: It is a 6-month period that usually starts when you turn 65.

During this time, you can not be denied or have rates increased due to medical matters.

This is what I call the "take it now or never" phase, as that could be true.

Answer: Simple, ask for their license.

Check it out on your State's DOI website or call them to verify.

That gets you half way there.

Last, repeat this with 2-3 brokers and you should be able to sense who is genuine and a good match with you personally. From there, it's not too complicated.

Answer: Don't be a hero.

Work with a broker.

We are free.

Get a broker, with many plan options, not an agent who represents just one company.

Answer: In my previous life, I worked as AV tech support.

A common saying in that industry is, "User error"

Not to defend insurance companies, but I do find a lot of frustration comes from not understanding what's in the box.

That's essentially what I do with clients. I read the instruction manual with them and explain it best as possible and from there, we are less disappointed than we may have been otherwise. No surprises at least.

It's not perfect, it's insurance.

Answer: Did you work with an agent or better yet a broker?

Did you do enroll yourself or avoid anyone that did try to help?

How did you enroll?

Answer: Solving the puzzle.

Connecting with people to help them tackle this complicated process and finding the solutions that are best for them is rewarding.

Answer: My joke is, the words insurance and best do not belong in the same sentence.

They are different, pros and cons to each, as is everything in life..

Supplements give you the most freedom and flexibility, but freedom is not free. Rising cost over time with supplements could lead to you dropping the coverage when you need it the most. This is the most reliable coverage with the least amount of restrictions, but overall the highest cost when looking at the G or N which are most common. Hi Deductible G could be a good compromise and competitive to advantage options.

Advantage plans can have lower costs, but come with more restrictions, such as getting approval for treatments and surgeries. I don't think advantage is all doom and gloom as many seem to propose, however, you are making a deal with the devil.

My rule of thumb is that, if the client is not too concerned about changing doctors in the future or not being able to access some facilities like Mayo Clinic in FL, as of recent, while looking to save money, then MA plans are viable.

My next rule of thumb is that unless there is 100/mo of savings, then MA plans may not be worth the restrictions. In that case Hi Ded G would be a strong option to consider.

Ultimately, use a hammer for nails and a screwdriver for screws, to get the best results possible.

Answer: Find a trusted broker and provide them all your current meds and any potentials if that's possible.

Let them do the research and wait for them to bring you a few plans to compare and save yourself a headache.

Answer: There is no doubt, MA plans are often pushed as they will provide the highest commissions for those enrolling into Medicare for the first time.

This is a fools errand, and if they are just neglecting the overall needs it will likely backfire, but it is a fact of the industry.

On the other hand, you may also ask, why don't agent/brokers inform consumers about High Deductible G supplements? Simply, money or commission.

So there are bad actors in all arenas.

Shop a few brokers and use your better judgments to see who is really taking your needs into account and solving it as best as possible.

Answer: This depends on what you have in place for Medicare.

For these two categories, Medicare Advantage plans have some of the best benefits you can get, where it is fairly common to find plans that offer around 2K of work potentially at no cost.

Outside of Advantage plans it's a bit limited as you would need stand-alone plans which usually offer limited benefits.

Answer: Generally, that is bad advice. Very bad advice in my opinion.

These are two different worlds with different objectives and really do not have much correlation in any way.

The only way this could be argued reasonably, is assuming you are at the age of Medicare 65 or older and in good health with your own savings already in place, then in that case paying for life insurance may not be the best use of resources.

However, it is not to say, now that I have Medicare, I do not need a policy to either cover final expenses or not have something to leave behind.

For both of those goals you really should be establishing those policies well before 65, ideally in your 30s-40s to get the most efficient and cost-effective policies which you would not just terminate since you have health coverage.

Often, seniors only start thinking about life insurance as they come into Medicare, and at that point your options are limited to unfavorable life insurance specifically for final expense. These are often overpriced for what they offer, but may be helpful for the family.

Either way, Medicare should not be a factor in deciding if that is needed, instead one should be proactive earlier in life to avoid purchasing low qualify final expense plans.

Answer: I offer a 20-30m presentation which I call "The 3 paths to Medicare" where I go over Original Medicare, Supplements and Advantage plans with the pros and cons of each path, general costs and important timelines/restrictions.

While Original Medicare is not typically recommended, I make sure that is well understood as it is the basis of the other two paths.

The main purpose is to provide general details and establish the vocabulary beneficiaries should know.

Afterward, I encourage them to do some of their own research such as read articles or watch videos that explain specifics now that they are generally educated, and those materials will be more helpful and make more sense.

From there, we have further discussions to answer their questions and go into specifics about the path that suits them best.

Answer: Yes, but they may not qualify for premium free if they do not have the required working history, which is about 10 years.

In that case, they would have to pay for Part A, but they or their spouse must also be a legal citizen or resident.

Answer: It will depend on a few factors such what type of coverage you have such as Medicare supplement or Medicare Advantage.

Generally there are 2 levels for appeals and each level can take 60 days, however if you have a Medicare Advantage they have shorter timeframes.

Answer: Yes, it does cover some chiropractic visits, but it is limited and must be medically necessary.

It will cover adjustments related to spine misalignment, but not services like acupuncture or massage therapy.

Answer: Part B penalty I would say is the most common significant one. This is a 10% penalty for a 12-month period that you are not enrolled or have other qualifying coverage when eligible. It is significant because it is a lifetime penalty.

So if you go 2 years without it and then enroll when Part B would be around 200/mo you would be paying about 240/mo instead, for life.

The most common may be the Part D penalty, which is 1% for each month you go uncovered after being eligible for 63 days. Even after 2 years, this penalty would not be too much of an increase so not as significant in my view, but I would avoid if possible as it is also a lifetime penalty.

The part A penalty would be the least common and least significant, as most people get A for free and if you are penalized it eventually goes away.

Answer: At the age of 42 I have come to the realization, don't be a hero.

Don't cut your own hair, don't do your own taxes, and don't do your own health and life insurance policies could be added to the list.

Sure, there are exceptions, but for the most part, let a professional do their job because they are experts and will make sure you get the best outcome possible.

Unlike a barber or tax pro, where at worst you lose a few hundred buck or don't leave your house for a few days, mistakes with your Medicare could be significant.

The best argument to use a Medicare Agent, is the fact that it does not cost you anything extra. In fact, you are essentially paying for them whether you use them or not, so you lose value when you choose to DIY.

I always tell people to shop brokers, not plans. I would speak with 2–3 brokers to get their recommendations. Not all brokers are equal, some may be more experienced, offer more plans or just match your personality better.

Also note, you want a broker, not an agent. Agents represent one company, brokers represent many. Your broker should help you compare options so you are getting the best coverage for the best cost.