1) I took an online class and it is a couple of tests about the basics. Very easy and not very time consuming. Back in normal times, I went in to a live class on Saturday to finish up and I think it was something like two hours and then a live shoot with .22s. All of it was very simple.

2) I'd think the simplest way is to apply for whatever unit your land is in, for the animal you want to hunt. There are private property only tags, but I don't have enough experience to guide you about applying. You can apply for one or the other, then choose the other option as your second, third choice. When browsing large PDFs, don't forget that you can sometimes use Ctrl-F to pop up a search bar, then type in the word or phrase you're looking for and scroll through every time that word shows up in the document. Sometimes that makes things easier. Finally, there is a website that shows you historical data for each area you want to hunt where you can find out about how many points it takes to pull a tag in that area, success rates, etc. I'd use that to see if your chances of drawing a tag change between just the unit your property is in, or if you want to go private property only in that area. Hopefully people with more experience will chime in soon.