You won't require another waiver on renewal, and a renewal H1B doesn't need to jump through the "no other workers available" hoops that original approval needs. As long as the company doesn't go under - as long as you get the original approval you'll be fine.

In regards to the 10 year ban, it will count from your last departure from US. So let's say that you leave in 2016 it will run out somewhere in 2026. Falling out of status will not affect that ban in any way. Also if during that time you marry a US citizen you can seek AOS together with an hardship waiver stateside.

If you entered legally I'd personally look into a marriage to a US citizen.

If you entered illegally then you can clear that using advance parole, even if there's no prospective candidates, travel on AP doesn't trigger the 10 year ban and that legal entry is yours forever. Also entry as a parolee makes you an "arriving alien", which is a strange concept that has its own rules, namely:
1) You can adjust status (via USC immediate relative, or 245(i)) even if you're in removal proceedings or subject to a final ban, however,
2) You do not have the right to have your AOS application reviewed by a judge if you get denied (with the exception that if you became an arriving alien via AP from said petition). (Like let's say you arrived on a B-2 visa and overstayed, married a US citizen, filed for AOS, you travel on AP that you got via the AOS application, a judge can review this AOS application but no subsequent one).

So let's say that Trump wins presidency and goes nuclear on us. You get an NTA, you can basically say fuck it, a few years pass - you marry a USC, you can adjust status despite an outstanding order.

I got your PM and will respond to it soon.