It all depends on how confident you are doing your own work. The difference may vary by builder and I'm sure some will chime in. A short block generally consists of the block rebuilt with bearings, rod, cam, flywheel, valves, guides, etc, no head fitted, no oil pan mounted etc. A long block will come with the head and pan on, bellhousing on and possibly a rebuilt ******. You must install the auxiliaries, i.e. distributor, water pump, generator, starter, carb, etc otherwise you may specify to the builder to give you back a drop in engine ready to go. Obviously, the price of poker goes up the more you have done and prices will vary builder to builder.
Best thing is check with local chapter members and get their opinions. Also, you have to make a decision to go with an original style rebuild (babbit, stock crank, etc) or opt for the new style, insert bearings, counterbalanced crank, lightened flywheel, etc, etc.
Stand by, your about to hear a lot of opinions pro and con.