I think you are right that the best long-term strategy would be to do the tiny home/shed. My finances to get started might not allow it, however. The cheapest pre-built shed I've seen in that area was $3,100 for a used 12 x 24. I could go a bit smaller and I wish I could build my own cheaper. But then it'll cost to wire and plumb and insulate and seal it off from bugs as well. I could easily blow my whole savings and not have anything for other projects. I could go the rent to own route with a new shed for like $1,000 down and $200 or so a month, but I don't like debt and paying tons of interest which really jacks up the overall price paid.

I want to keep my housing budget under $4,000 so I have enough left over for chicken wire, fencing, etc and some stability paying bills for a good while. I'm also not sure how much I will be able to sell my place in Illinois for. If I have to drop the price some more, that'll impact my situation.

So I'm still thinking I'll just make the smaller bedroom in the front livable and sealing it up so I've got a comfortable place to sleep and work on the computer. Just keep my food and cooking stuff in plastic tubs so the bugs don't get to them. Then next year buy a shed and start turning it into a cabin little by little as funds allow. Another thought was to buy an older RV/travel trailer in the $3-4k range to live in until I could get a cabin built. That seems like a waste of money in the long-term, however, as I probably wouldn't get much back for the RV when I'm done with it.

Lots of ins and outs and what have you. Maybe I'll find a couple grand worth of junk in there to sell, there is a piano and that ham radio tower has to be worth something. I am enjoying all these math problems to find what might work best, that is fun for me. Thanks for your input, I really do value hearing other perspectives as I sort through my options.