My ultimate goal is a street warrior. Not full out max HP. Total sleeper.

I guess my concerns are more based on a lack of knowledge on the 4200/4L60.

Either direction will cost about the same with similar power output, though the 250 will be at the top end of its life and the 4200 more mid-life.
I've no intention of touching the internals on the 4200 (at this point) as I read and hear they can handle 15 lbs in stock form.
So a built 250 will have about the same output as a stock 4200. Seems an easy choice, so why am I having such a hard time with it?!?

Very rough cost breakdown is like this...

250
Head - 1000
Pistons - 1000
Machine shop - 1000
Rad - 400
Plus miscellaneous.

4200
Buy engine, Trans, rad, drive shaft, wiring harness, computer - 800
Break the wiring and flash the computer - 1000
Exhaust -500 (includes me making the up pipe and down pipe)
drive shaft - 3-500
Plus miscellaneous for this install etc.

I didn't include the fuel system, meth injection, frame connectors and random things that apply to both builds.

Now that it is written down again, it does appear to cost less going with the 4200. I'm sure there is a lot that I have overlooked!