I think the coexistence of ad supported plans is orthogonal to the above. E.g. Netflix still has an ad free plan, regardless of the other plans, but Google gives you no option.
"And now let's introduce this video's Sponsor, SpywareVPN"
Yeah, sure, "ad-free plan". As long as you don't watch (what feels like) the majority of videos on the platform.
I pay for premium, but I'd gladly pay 4x as much if Youtube also required creators to mark sponsored segments and let them all get skipped automatically if you paid for youtube "double premium double ad free" or whatever.
The premium plan actually gives you a little button to fast forward sponsor segments. (Not sure, if that's also on the free plan?)
You are right, that you still need to hit that button. It would be need to trigger it automatically. As far as I can tell, creators already tag the relevant segments as sponsored for other legal reasons.