Oh God, definitely don't pick the flight through PEK.

In addition to the alternative of bullet train to Shanghai then transfer, you missed a third option that in some respects might be easier: direct Airport coach from Hangzhou to Pudong. IIRC, the first bus is around 06:40 or 07:00 from the Huanglong Tourist Center in Hangzhou, takes about 3 hours to get to Pudong but delivers you and luggage straight to airport terminal. As long as I could get a bus out by 07:00-ish, this is the method I personally would choose just to avoid schlepping suitcases on train-road/subway transfers in Shanghai. This coach will bypass central Shanghai so morning traffic isn't likely an issue.

And then there is the expensive but highly flexible fourth option, which is private car all the way from Hangzhou to Pudong. Maybe if you're on expense account.....?

Answers to Questions:
1) see above
2) try the user friendly http://www.travelchinaguide.com/chin...from1=Hangzhou. I'd take a train leaving by 07:30 and you'd want a G train to Shanghai Hongqiao since that can connect you to the Airport Shuttle bus to Pudong. Or grab a taxi. I wouldn't subway this to PVG.
3) so noted
4) yes but depends on incoming flight being on time....and that is a dice roll I personally wouldn't take, given your restriction in comment #3.
5) no. you'll have airline check-in at the Biz class lines but you get no special privileges at Immigration or security. However, the Chinese are fairly efficient at processing people through. However, since you're flying to the USA, and on a US carrier, expect an extra security check at the gate area, probably with a cursory manual search of your carryons. They should call high level elites and premium classes for boarding first.

In summary, if you arrive at your Pudong Airport departure terminal by 10:15, you will have time to check in and jump through necessary hoops to make a 12:10 flight with ease though likely not much lounge time.