So let's say I go through and warm a bunch of the homesteading badges and what have you. I get to a point where I know good and well I could run 50-100 acres no problem. How do I make Otis down the street aware of this without coming off sounding super thirsty for him to give me his land? Would a classified ad in the local paper be a good idea simply indicating I'm looking for land to inherit? Have any of you been successful SKIPping? How did you manage it?
I think one way to do it is to put yourself in a position to be known by as many Otises as you can. Either by joining clubs/organizations they are in or by dating their daughters or meeting them at church. If they meet you and take a shine to you, there's a better chance of the magic happening. Of course, posting here on permies is another way to do that as well.
Another related way is to offer to do work for them for free. Maybe some BBs. Tell them you're doing this permaculture program and need to do projects. They get the fruit of your labor and hopefully you don't break too much stuff in the process. Then they might get curious about PEP and the magic happens.
There's a good chance that the older they are, the more likely they are to need help. And if they have help already (kids, etc) there's a good chance they won't want to will their land to non-family anyway.
I kinda doubt you'd have much luck by directly asking or putting up an ad.
"Hundreds of years from now it will not matter what my bank account was, the sort of house I lived in or the type of car I drove... But the world may be different because I did something so bafflingly crazy that it becomes a tourist destination"
Stop it! You're embarassing me! And you are embarrassing this tiny ad!