@Nickkaderli, " It seems like I’m in the current version of you from the 60s, and you the future version of myself." Wow, make me feel old!
Actually, I've had a pretty good hunting life, and along with 50+ years of great hunting memories, I have a house full of trophies to spark those memories.
Looking back, there were a lot of things that I should have done differently...Like all of those years that I bought an OTC Montana Bighorn sheep tag and I would hunt the opening weekend, and not go back even when the season was 3 months long and the quota of rams was not taken. Now there is only a fraction of the number of Unlimited Sheep units, and the quota is filled in most of them the first week. Or the years that I bought an OTC Montana Grizzly tag and most of my Grizzly hunting was basically limited to just hoping that when I went back to get the meat, I would find a bear on the gut pile of an elk or moose that I had shot. We will never see another OTC Grizzly tag in the lower 48.
And like
Bocajnala posted, "Tag availability and price for some of the hunts that require guides will be your biggest hurdle. " When I drew my first Montana Mountain Goat tag back in 1976, I had a 25% chance of drawing a tag in that area. Now there are no tags in that area, and most of the Montana Goat areas have less than a 1% chance of drawing a tag. In 2017 I was one of the last non-resident hunters to shoot a Caribou in Quebec before they closed Caribou hunting to non-residents. My DIY Montana Bighorn sheep, Moose, Goat and Elk hunts all cost me less than $100 each (tag and a tank of gas), where guided hunts for these animals can cost from $5,000-$20,000 or more for each of these animals, and I have seen Desert Sheep hunts advertised for up to $80,000.
I do not have a goal of taking all 29 animals of the North American super slam, but I do like hunting new and different animals and in new places. I'm hoping to add 3 new ones this year.
Good luck on your quest.