Have you tried the 36t yet? With an out of the box 2 stroke you will really be bogging the engine going up a medium hill. I'd get a expansion chamber muffler first cause you'll need the extra power to pull the smaller sprocket. I got the Spooky Tooth one, it boosted my speed about 4 mph on the hills w/ a 44t and after riding 1700 miles in 3 months I'm happy cruising at 30 mph.
I may go with a 40t cause I don't think it will hurt my take off too much.