After reviewing the stats of every skater I think it would be very wise to go for Jamie Thomas as the skater of choice. This is because Jamie can handle the big drops since he has the best landing stats available from start out of all the skaters. He is also on par concerning speed, which is set to 6 from the beginning.
Because of these starting stats it is possible to kiss the rail at the first half-pipe in the hangar, ollie, grab the cash, and make the landing without bailing.
In the test I did playing with Tony Hawk I had to take an alternative route in order not to bail upon landing. In that play I go up on the lamps close to the ceiling, then I have to land in a grind over the half-pipe in order to keep my points and not bail.
With Jamie I would not need to get up there at all. Just grab the cash as you're coming down from the start.
Not sure what stats to upgrade after the hangar yet. Speed is of course very favorable throughout the entire round. Any thoughts on stats-distribution would be very helpful.
I might go ahead and record a test run of the hangar with Jamie to see how it compares to Tony's run.
Edit:
Tub told me on IRC that he had a 100% speedrun for THPS2 on his hard drive. Didn't get a response from him after he said that, so I went ahead and found it by googling instead. The download link can be found on this board:
http://forumplanet.gamespy.com/tony_hawks_pro_skater_2/b50195/9425240/r9425252/ along with some comments. Good to analyze routs and ideas. Thanks for sharing Tub!