How is that supposed to happen, exactly? I still use plenty of software which was released before Bitcoin even existed. Wallet software won't simply vanish if people find it useful, make backups of it and continue to use and distribute it.
Hell, I'm sure I've got backups of relatively useless software that I don't plan on ever using again. There's still a MultiBit installer kicking around one of my drives here somewhere. It certainly wouldn't be advisable to use, but it would still (just about) work if I was left with no other option.
Yes, I agree with you. However, I observe a mass adoption of the newer address types. In fact I have a PK that gives me access to a legacy address, that's why I felt the need to ask.
There's a lot of niche things quite a few wallets support that I think would go first (like mini private keys and p2pk - which I assume is still possible).
To be honest, now that I think about it more clearly, I don't see the reason why they would stop supporting legacy addresses. I mean, even if they are deprecated, they still don't provoke any issue to the software developers, nor to the product they produce. They could potentially just exist.