I found a 1998 Vortec 350 w/102K miles. Supposed to run good but does have a slight tick. Guy wants $200 for it and I would expect to tear it down and fix what ever is wrong if not do a re-ring and new bearings while I'm at it.

and? dime a dozen.just the motor? no wiring or pcm or the related? i picked up a 5.3 in good shape with a 2wd 60e and full wiring harness and pcm for 500$...81K miles on the motor.
stay with the vortec. just be aware theres a few things involved. Intake, larger tbi. custom prom, ect. once its right, you wont regret it though.I have not completely researched it, but I'd have time to work around the issues... My other option is dropping in a stock 6.5L turbo diesel as well though. I'm not in any rush to buy this motor, just starting to put some #'s in my head of what my options will cost mainly.
The $200 price is decent. Are you looking to run the 98 injection or the 91 injection? This will make a big difference in price and legality of the swap.
How does it affect cost and legality specifically? Just Curious.
and its a newer motor with less miles, more power, more potential, and totally complete and didn't need a rebuild...and? dime a dozen.