tranny for my 86 c 10 2wd

[i heart square bodys]

i am stuck between a rock and a hard place with what i want/need to do with my tranny. in my truck at the moment its a TH350S ( "S" i guess had a bunch of extra crap that is not acctually hooked up on my truck such as lockup converter) i am dropping a 1968 327 into the truck with a mid idle cam and someday I want to go to a bigger cam so i will need a stall coverter for an auto. im stuck between a 700R4 or some kind of 5 speed that would work good, i really know nothing about standard tranny's at them moment. a 5 speed is what i have wanted in it but i dont what it takes to get one into the truck and if it is really worth it. from anyone that has done a 5 speed swap what will i need to know ?