Hey Tyler, how's the Black Bear tuning coming or do you have it now? (if you have it, ignore the rest)
Sorry I haven't been on here (I realize it has been 2 months since you started this), but here's what I know.
1) Scotty is right. You would have wasted $50 by going to an in-person tune. Justin can't do '96 or '97 (I think) in-person. - We had a guy with a '96/'97 K1500 that Justin had to send home (luckily he was only 45 miles away so at least the guy didn't travel far).
2) I thought TM started when the Vortec engines and 4L60E came out, but I might be wrong. Either way, if Justin does ask, go with something between 75 and 85% or maybe just ask him what he did for mine (tell him Matt from the Rogers, MN tune in April).
3) Go with the "Standard" shift option. I like it a lot. My truck drives as though I only have the Corvette servo installed at part-throttle under normal acceleration, but firm at like half and at WOT it shifts harder. At WOT, I chirp the tires on the 1-2 shift and on the 2-1 shift if I step on it and and going at the right speed.
4) As far as octane goes, for the extra $4 it costs me to fill up with 91, I justify it by having a kickass, 2.5 ton truck that is a blast to drive. If you don't want to spend that much extra on gas, at least go with the 89 tune. I know one guy, LIFTED_GMC from GM-Trucks, changed his mind just before Justin left and changed from the 87 tune to the 89, but I haven't seen any info from him as to how the truck has changed.
You really don't need to worry about the super specifics. Justin asks you what you want the truck to do and what you use it for. So other than TM, shift firmness, and octane, you don't have to worry about a thing.