Your Benefits,Simple & Clear.
Theo Hill helps seniors across the tri-state area find Medicare plans that actually fit their lives — at absolutely no cost to you.
Plans for every stage of life
Tap any option to expand the full breakdown — best for, what's included, things to know.
- People who want one combined plan, not multiple cards
- Those who use providers in the plan's network
- Anyone wanting extras like dental, vision, gym, OTC
- People comfortable with copays over premiums
- Hospital & Medical (Parts A + B)
- Prescription drug (Part D)
- Dental, vision, hearing (varies)
- OTC allowance, gym, transportation
- Annual out-of-pocket maximum
- Uses provider networks — confirm your doctors are in-network
- Plans change yearly — review every AEP (Oct 15 – Dec 7)
- Not ideal for frequent out-of-area travelers — consider Medigap
- People who travel often or live in multiple states
- Anyone wanting predictable monthly costs
- People who want to keep any Medicare-accepting doctor
- People with frequent specialist visits or chronic conditions
- Plan G — covers everything except Part B deductible
- Plan N — lower premium, small copays per visit
- Plan F — eligible if you turned 65 before 2020
- High-deductible G — lowest-premium option
- Higher monthly premium — but lower out-of-pocket when used
- Doesn't include drugs — you'll need a standalone Part D plan
- Easiest to qualify during your 6-month Medigap Open Enrollment
- Enter all your meds, doses, and pharmacy
- Compare annual cost across every Part D plan in your ZIP
- Find cheaper generics & preferred-pharmacy discounts
- Re-shop every year — formularies change annually
- Late enrollment without creditable coverage = lifetime penalty
- Most Advantage plans include Part D — don't double-enroll
- Extra Help (LIS) may dramatically lower your costs
- For Medicare + Medicaid recipients
- $0 premium, $0 deductible, $0 copays on most services
- OTC / grocery / transportation Flex Card
- Personal care coordinator assigned to your case
- For diabetes, cardiovascular, end-stage renal, COPD, etc.
- Network built around your specific condition
- Often $0 for specialist visits, supplies & meds
- Year-round enrollment for qualifying conditions
- Preventive: cleanings, X-rays, exams (typically 100%)
- Basic: fillings, extractions, root canals
- Major: crowns, bridges, dentures, implants
- Annual maximums vary — we compare carriers
- Annual comprehensive eye exam
- Frame & lens allowance every 1–2 years
- Contact lens allowance (in lieu of glasses)
- Discounts on LASIK and progressive lenses
- Pays $100–$500/day per hospital admission
- Cash goes to you, not the hospital
- Add-ons: ambulance, ICU, observation, outpatient surgery
- Low premiums — typically under $40/month for most ages
- Medicare Advantage plans with hospital copays
- High-deductible Medigap plans
- Anyone with known chronic conditions
- Fixed-income retirees worried about a hospital stay
- No medical exam — health questions only
- Available for ages 50–85 (carrier-dependent)
- Cash value builds — can be borrowed against
- Tax-free payout to your named beneficiary
- Funeral, burial, or cremation
- Outstanding medical bills
- Mortgage, car, credit-card balances
- Any final wishes for family
Theodore "Theo" Hill
Theo founded Uphill Benefit Group after years of watching family and neighbors get pushed into the wrong Medicare plans by call-center agents who'd never see them again. He built Uphill to do the exact opposite.
As an independent broker, Theo isn't tied to any single insurance company. He compares plans across 12+ major carriers, walks you through the trade-offs in plain English, and helps you pick what genuinely fits — not what pays the highest commission.
- Independent — works for you, not the carriers
- Zero broker fees — always paid by the insurance company
- Specializes in dual-eligible & D-SNP clients
- Personal support long after enrollment day
- Spanish-speaking support available
REAL STORIES
Hear It Straight From Our Clients
Short clips from real families Theo has helped find coverage that actually fits.
Talk to Theo — 20 minutes, no pressure.
Pick a time below and we'll review your situation together. We'll look at your current coverage, prescriptions, doctors, and the carriers that fit best in your ZIP code.
Pick your time
All times are tri-state · DE / NJ / PA
Plans from every major carrier
As an independent broker, we compare across 12+ carriers — so you always get the best fit for your situation.
Medicare made simple
Still have questions? Call (302) 496-4619 — Theo answers personally.
Medicare Advantage (Part C) bundles Original Medicare with extras like dental and vision, often at $0/month with a network of doctors and copays per service. Medicare Supplement (Medigap) works alongside Original Medicare and pays your share of approved costs — higher monthly premium but very predictable bills.
Theo walks you through both based on your doctors, medications, and travel habits.
Nothing. Our service is 100% free. As an independent broker, we're compensated by the insurance company when you enroll — at a CMS-set rate that's the same across every carrier. We have every reason to find you the right plan, not the most expensive one.
Ideally 3–4 months before your 65th birthday. Your Initial Enrollment Period starts 3 months before your birthday month and ends 3 months after. Starting early avoids gaps and late penalties.
You may qualify for a Dual Special Needs Plan (D-SNP) — one of Uphill's specialties. These plans offer coordinated care, $0 premiums and copays, plus a Flex Card for OTC, groceries, transportation, and utilities. Call us to see what you qualify for in your ZIP.
Yes, in certain situations. Special Enrollment Periods (SEPs) apply for qualifying events like moving out of your plan's service area, losing employer coverage, gaining Medicaid, or being diagnosed with a chronic condition. Theo can confirm whether you qualify.
Theo asks about your doctors, medications, pharmacy, travel plans, and budget. Then he runs that through our carrier comparison tools and walks you through 2–3 plans that genuinely fit. You don't sign anything on the first call unless you specifically want to.
We can't guarantee specific plan availability, premiums, or benefits — those are set by the carrier and CMS, and they change yearly. What we can guarantee is that we'll look at every available option in your ZIP code honestly and present the trade-offs in plain English.
Let's find the right plan, together.
Book a free 20-minute call with Theo — phone, video, or in person across DE, NJ, and PA. Zero pressure, zero cost.