SSDI w/ Medigap vs. Medicaid

Hi folks, have tried going through past posts to find more info but struggling to find a clear answer. 😭 Hoping y’all might help me understand my options better!

• Located in Oregon, urban metro area

• On SSDI (age 41), unable to work, spouse is self-employed and on Medicaid

• Have Medicare A/B + D, with B premium paid by Medicaid and D with no deductible / tiny copays

• Dual-eligible with Medicaid and Extra Help through April 2027 (can’t get kicked off, phew)

• Am a walking pre-existing condition (see SSDI lol)

• Yes, met with a SHIP counselor (was some help but wasn’t really able to give me a straight answer about the questions below)

Okay, so, here’s where I get stuck…

• If I keep my current setup, I have the absolute best combo of getting to see all my doctors, not having to deal with Part C / MA nightmares (PAs, denials, in-network BS, Rx hassles, etc.), and basically pay nothing but nominal Rx copays. Seems like the dream, right? For now…

• Buuuut, knowing that I’ll likely lose Medicaid next spring when I reapply, am I hosing myself not just sucking it up and paying for a GI Medigap plan while I still can, since 65 is a long way away for the next GI enrollment? Is it penny wise and pound foolish to be cheap for a year but then pay for it for the next decade because I can’t get anything but maddening Advantage plans that I have to constantly fight with for coverage? Am I wrong about not being able to get GI enrollment again if/when I lose Medicaid?

Many thanks in advance for your knowhow! 🙏