How reliable are HWs in terms of holding funds for long term (maybe 5-6 years into the future)?
I can tell you that my hardware wallet is working fine even after 2+ years. You can also ask yourself how reliable are you in keeping your wallet physically intact? I still have old Siemens mobile phones that I used long, long time ago. They work, just fine if it weren't for the battery. One of my best friends is as clumsy as they get, he can't hold onto anything and switches phones regularly because the dickhead keeps finding new ways to break them.
My point is, if you take good care of it, it will most likely work for many years. Ledger has in the past replaced wallets even after their warranties expired + there are regular discounts and promotions where you can get a spare one for cheap.
To be honest, I'm still using legacy addresses cuz the segwit stuff confuses me.
You don't have to understand the technical aspects of the addresses. Just know that you will save on transaction fees, and that should be enough.