New to this
 

i have an 86 iroc with 305 v8 i want to swap the motor but i don't honestly know if it is more economic to build a 396 V8 or just purchase a crate motor, also don't know what type of transmission would work with said motor. i already know i will most likely have to get better suspension and rear dif. though

If you have a 305 TPI it is easy (???) buy a long block 350 and transfer the TPI and everything else from the 305. You will need 22# FI, Knock sensor and a new chip for the ECM. The 700R4 auto will bolt up and the 10-bolt rear will be fine. Tons of material available on this swap. Suspension wise you can work on that after the swap is up and running. One project at a time.

I agree with Black on this. Don't want to much going on at once it can become overwhelming and cause a lack of progress. Ask me how I know this. LOL.