Hi Mike - your looking @ a pretty easy swap just make sure you get all your ducks in a row. I assume your just lookin to build a street cruiser with a little more HP (how much?) The 3.08 gears are bothering me with an OD trans. With 20 in wheels your tire dia. is going to be in the 29in range which will put you around 1700 rpm @ 70 mph and you would have to walk softly on the engine build. A non OD trans would put you in the 2500 rpm range. Options have been brought up on the block and yes a roller is better than flat tappet BUT I am hearing budget and a roller is considerably more. Almost all my builds have been flat tappet and have never wiped a cam. Keep in mind that your drive train components need to complement each other. Buy this I mean your intake, carb, cam, converter, and rear end have to be sized right for hp and rpm you want to run. I think if you put pen to paper as to how much parts, machining, and time will be, a crate engine isn't a bad choice - done w/ warranty.
To bad you didn't lived closer to me I have an couple engines and 4 sets performance heads that might have interested you, due to health reasons I'm been trying thin out my parts - my poor Regal hasn't been out of the garage since a year ago Memorial weekend.
350 CHEVY - $500 (CANTON)
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I have a 350 chevy 010 block w/ standard bore 4 bolt. Forged steel crank std/std which I sent out to Moldex to be checked and polished. Chevy x rods w/ domed pistons. Has a comps 306s cam w/ lifters all kept in order and a double roller timing set. Flywheel, melling 55hv oil pump, damper, oil pan and timing cover. $500.00 for all. Also have other SBC parts and 4 sets of performance heads