Advice on small block (and transmission) shopping?

You will get 8 gazillion different opinions on what's best, the best thing to do is first determine what you are going to be doing most with the vehicle and then plan according to that goal while keeping your budget in mind. Take the time to research all the suggestions and then make your parts choices.

Here's what running in a 64 Dart used primarily as a daily driver that has some decent power and attitude:

'77 360 LA motor, stock bottom end, stock heads with EGR ports tapped and plugged
Holley Street Dominator intake
Lunati cam 288 adv duration ([email protected] I&E) .480" lift
1.6 roller rockers
Holley 4777 650 cfm double-pumper carb
Shorty headers with 2.5" dual pipes and flow master 40-series mufflers
Rebuilt A999 (heavy duty 904) auto with shift kit and 2200stall converter
A-body 8 3/4 with 2.93 open gear (good highway gear!!)

This is a fun driver that sounds great and with the taller gear cruises on the highway at 65 all day at roughly 2600 rpm. Motor combo dyno-ed at approximately 325hp at the crank so it's not a full on strip killer but plenty enough power to have fun in stoplight action on the street.