I do not even consider a 355 much of an upgrade in performance. 5 cubes is nothing and not even worth punching that small unless its just for cleanup the walls, its no performance increase. You could build a stock bore and a 355 the same way and see very little incrase in power, if any, surely not enuff to justify worth the extra money for machining.
http://www.popularhotrodding.com/features/0611phr_vortec_small_block_350_chevy_engine/index.html This is the route I am most likely going......with some small changes......
383 Stroker... I would be leaning towards the 383 with about 325hp., but, 425ft. lbs. torque. My biggest thing is something I could build on in the future, if the bug really bit me again(to go faster). As as little side bonus the 325hp. only requires reg. 87 octane gas @ about 9:1 compression. I know it is the truck version(torque and all) but the car will finish out around 4000 lbs.(cost is about $2900. from (g+$dwinch with a warranty). As far as a 355, not really an option, just not enough advantage to mess with and no reason to (better options). However I still am checking out the LS/LM option. Unfortunately someone hinted that the strokers wern't that daily driver friendly. They never got back with me, to completely explain their reasoning. The tranny thing is still a very much 'in-the-air' thing. Like I said, I really want to use a his/hers in a floor console, but no specific person(in the know) has said that they can do it with the 3 speed shifter. So, I'm still searching around. The tires will be around 26.5 to 27" tall (15"x7", with a 225/60/15 or maybe a 235 if I can keep them from rubbing without sheet metal work). So the 3.73 gear shouldn't be an issue (rpm wise). Thanks guys, I really apperciate the input !!! Bruce