Here's a big tl;dr, basically I found a mechanic at a big shop who was actually helpful and fair and didnt price gouge me and wow really just mind blown. Wanted to say thanks.

---tl;dr begins now

Had a pretty good experience at the big nationwide chain bike shop a few days ago. They were having a decent sale and I was cleaning up one of my old rigid MTBs (Trek 820, loved that bike) to give to my little brother as a birthday present, so I was in there buying a few tires and knick knacks.

Picked up a Vittoria cross tire to throw on my steel geared bike and long story short the ***** was just too small (700C on a 700C wheel, but Vittoria's dont seem to stretch great anyway and this was a 20+ year old made-in-italy rim... they didn't play nice). I got it on with a tube but literally had to use a mini-crowbar to get it in place, and the tube was unsurprisingly pinchflatted in like 50 places.

Took it into the shop to get my "flat" fixed and mentioned that the tire was almost impossible to mount. Mechanic said $15 for labor and price of a tube, and I said sure because otherwise I was cutting off the tire myself. All told she spent almost an hour working on the tire trying to get it off and then re-mounted and finally let me exchange the Vittoria for a Panaracer which fit much better, even though there wasn't anything defective about the Vittoria. Recommended some better tire levers than I'd been using (her favorite pro racing for a few years, apparently). Still only charged $15 for the labor even though it ended up being way more than a regular flat fix.

Only ended up paying $9 out of pocket including the levers, since the vittoria was more expensive than the panaracer and I got full exchange for it.

Basically, I went to get something fixed at a big-box bike shop and it was LESS EXPENSIVE than if I'd done it myself; it would have run the full $$ for a different tire even if I'd gotten the vittoria off without cutting it, which isn't likely.

Mind. Blown.