I wish I could help more, but I don't know much about the landowner preference, other than that you have to own a minimum amount of land to meet the requirement (160 acres?) and that if you do, you have a better chance of getting a tag.

They hold a drawing to determine who gets licenses, because for most of the big game, you can't just go out and buy one, you have to apply and hope your application gets drawn.

If you're unsuccessful, you should get 'preference' next year, meaning you'll have a better chance of getting a tag. The more years you are unsuccessful, the more 'preference' you will get, so that people can't get unlucky and go years and years without getting a tag.

As for the out of state aspect; I can't really help with that, as I've never dealt with it. I lived out of state for a few years but never hunted back here at the time.

Good luck with everything!