Both are nice to have, stiff boots for steep nasty stuff and heavy packs, lighter boots for everything else. If your trying different boots out, keep an extra pair or two in the truck.
Wisconsin, find some public areas that have been logged in the last few years. Wont exactly be spot and stalk but the larger tracks of land you could find a few areas that you could.
Iv picked up a couple leupold vx-3’s on gunbroker for around that $400 range before, never had any issues with them. I also have been hearing a lot about arken optics being good scopes, but no personal experience with them. Maybe something to check out.
Id go with send it and figure out the rest later. You can always watch where they bed or what direction they head and figure out a way to go after them when you think you have a little bit of time. At least find the elk first.