which year best 360 to start with?

Robb, good thinking. On a low performance side of it, yes. Making room for a 2.02 or upgraded set of valves is an extra expense along with hardened seats of something older. (Thinking race side of it all. or heavy street fighter.)

A 1.88 is very good for the street. It can provided enuff flow for a good engine. Back cutting the 1.88 is a inexpensive way of upping the level with some bowl porting and etc......