Welcome to this forum, M. (Name?) You'll find many a worthwhile opinion to consider here.
As you can already see, there is much to research. Your initial challenge is that you lack a knowledge of and a perspective for any aspect of recreational flying and a/c ownership. Nothing wrong with being ignorant or inexperienced, and of course that's why you are inviting information. The snag is that A's to your Q's need to be yours and not some collective distillation of others. So I'd encourage you to put your main initial emphasis on learning to fly. Life long dream or not, not everyone actually enjoys flying. Or feels comfortable in a tiny a/c in the midst of a big weather system, or perhaps when that a/c lacks a heating system during a cold snap or is bouncing around in summer heat & humidity. Find an instructor and rental LSA a/c - which may prove much harder than you imagine, depending on your location - and let's see how you feel post-solo and after mastering some of the regs and procedures. For your location, this is the perfect time to begin with the whole summer left to complete the license and check ride.
You may be able to find some other posts here on folks who've created their own 'airport'. Try the 'Search' function. But just in that category of Q's, here are some things I'd be thinking about:
-- get the airport directory for each of the state's you are considering from that state's DOT Aviation Department. Some states place great emphasis on getting private fields registered with the FAA and they publish basic info on them including contact details. They usually also publish an aviation chart for the state (may be digital and/or paper). Those sources would allow you to talk with some airstrip owners where you are considering living, no doubt your best source of information on what's involved in actually owning an airstrip. I had a long talk with a farmer/pilot on Saturday, listening to him describe the challenges of keeping his thresholds clear as increased electrical demand created a need for larger transmission lines which in turn must be placed higher. The concerns of an airstrip owner are almost infinite.
-- due to aging pilot demographics, we (the RAF; see my signature line) are finding many airstrip owners who no longer fly, want their beloved airstrip to remain in use, and are looking for someone to take it over. It's really quite amazing...and this also consistent with the many open lots and unsold homes for sale on commercial air parks where I've been speaking. Given how flexible your plans are, I'd be pretty amazed if you couldn't come across multiple opportunities to buy a strip of land with its own small airfield, and with an owner willing to bargain. Also, some private airstrip owners are eager to share their strip with a few others as it helps keep their costs in check, and that reduces the issues you'd have to face if starting from scratch.
-- along with a bazillion other factors, I'd favor WI over IN or MI because WI has amended their Recreational Use Statute to protect landowners with private airstrips from liability claims. Imagine someone seeing your little strip, thinking they need to practice a landing on grass, and then rolling their plane into a little ball of aluminum because the field was too short, too wet, too rough, etc. They wouldn't have asked you first about landing there, you wouldn't even know to warn them off. This is a common concern of private airstrip owners. More on this here:
http://theraf.org/news/2010/update-stat ... n-aviation
There's a good deal more to consider. But my suggestion is to dig into the other aspects as your spare time allows while first concentrating on getting some instruction plus study, ground and in the air. That will help you at least begin to define the kind of flying you want to be doing...and defining the mission is the first step in choosing an a/c to own. And that in turn will help shape the kind of airfield/airstrip/airport you'll need. It's a long process...but full of joy, too.
Good luck to you! It's great to see folks new to aviation that bring your long-held interest with them.