And with the engine, with the help of ck5 and replacing/upgrading parts, why couldn't i get an engine running?
multiple reasons. Most having to do with picking the engine to begin with. could have a broken crankshaft, scored bores, cracked cylinders, could have seized lifters, spun bearings, etc. etc.
rebuilding an entire engine may well require machine work, which aint cheap, so you have to be prepared for that. and even some of the work youll be doing yourself may well require you to spend even more money on specialty tools.
now you're interested in a 383 conversion, which involves a very involved process of selecting camshafts, calculating compression ratios, determining valve to piston clearances, combustion chamber volume, gasket volume, volume "in the hole" piston dish or crown volume, more block machining, etc. etc.
swapping in an engine can be a simple bolt in process... finding a junkyard gem and doing a full rebuild/modify project is a big bite to swallow if you're just learning the mechanical aspects of working on cars/trucks.
course thats all just my opinion.