Welcome to the madness!

You came to the right place, tons of knowledge here and lot of helpful people.
"The fuel tank leaks a bit, but after looking at the underside, it may be a drain plug gasket." Your fuel tank is most likely rusty and has a lot of pinholes. I used a POR15 fuel tank repair kit on mine 20 years ago and it's still holding up! You will most likely find some ammo when you pull your tank, lol, along with a lot of gunk that tends to collect under the tank causing the rust.
"All of the rubber from the hoses to the door seals to the windshield wipers needs to be replaced" Not surprised, you might be able to bring back some of the seals by soaking them in 303 protectant, Meguiars protectant, some people swear by ATF and some use heated water and wintergreen oil to restore rubber. Some replacement parts are expensive or Ubotanium so you might want to try to save what you can.
"Are there better options than the Haynes Repair Manuals for guidance?" Yes, the factory service manual. I'm pretty sure the links that were posted here were removed by toyota, but you might be able to still find some online. There are always some for sale on Ebay however.
"Also, I don't want to start a holy war, but based on the bumper I have, what winch would folks recommend?" Lots of people love the Badlands winch from Harbor Freight. You didn't really show a decent pic of the bumper, but it looks like it was constructed to move a herd of buffalo.
Rather than try to figure out what the heck is going on with that motor, carb, ignition system, etc. I think you would be better off yanking it and shoving in a newer 2f with the carb, ignitor, and all other "bolt on's" still attached. The license plate bolted onto the exhaust manifold pushed me over the edge, lol. Before you do that though, I'd change all the fluids and just drive the crap out of it. I think half the 40's that get torn apart never see the road again!
Good luck, keep us updated!!!