Well, it looks like you've got about all the advice you need, and at this late date you might have already taken the plunge. I'll use this post as a short test of whether or not there is continuing interest, and elaborate upon request.
I spent a few years "shopping." I finally got more serious this year, and spent a lot of time on-line, hoping somebody might offer to show me an airplane and maybe give me a bit of a ride. Didn't happen.
But I kept on a-truckin' and went through a lot of what you other shoppers are doing, but finally ended up buying a newly-almost-completed EAB STOL light sport category airplane, which will require me to fly the 40 hours of Phase I testing. The plane I bought was about number four on my list.
The first plane I tried to buy was a nice Kitfox-4 with a 100hp Rotax. The guy named his price and I agreed, but when I came back with the money, he backed out.
The second I tried to buy had actually become number one on my list, a Just Hilander with the 100hp Rotax. I negotiated this time, and we agreed on a price; I sent the down-payment check. The owner called a few days later and said "I've decided not to sell. Do you want me to tear up the check or send it back?" He was rough about it. Then I got a call from a dealer who specialized in that particular aircraft (with whom I had spoken earlier), and the dealer said that [he or she] could get the airplane for me, but it would cost me another ten grand. I declined.
So then I went on a long trip to see Highlander owners who were willing to show me their airplanes. The first one I visited told me about a CH 750 for sale up the road a fer piece, and I called the number he gave me. The man on the phone was very busy and I had almost decided not to look at it, as I had decided on the Highlander (rag and tailwheel and performance). But I decided to have a look at the 750 anyway, so I just drove to its location and hollered through the fence. Well, it turned out to be a beautiful piece of work and it had an IO-240 and a good, standard panel with enough room for a small tablet if I wanted a kinda-glass instrument later. So, I went for it. Reasons: Workmanship, workmanship, WORKMANSHIP. Power, power, POWER! New, new, NEW. The price was a bit above my upper end (which was about where your upper end was). Now, after some training by a master CFI, I'm gonna learn a lot, and become a test-pilot too--more or less. The paperwork, the dealing with the FAA, and a thousand other things that flesh is heir to, would have deterred me, had I known in advance, so I'm glad that I was ignorant of all that stuff. It is, and it's going to be, an adventure!
No, the plane's not my first choice. My first choice would be lighter weight, with lots of power (this one has enough), at a lower price. But maintenance is not likely to kill me, and the resale value is likely to hold up well, should I later find an ideal Rans or Highlander for the right price. And, the experience I've had with the people involved, unlike the first two, is priceless! (So watch out for people! There are not-so-good'uns and some exceptionally fine one out there in airplane-land.
As you've been advised, consider what you'll have to spend AFTER the "honeymoon." The operating cost, not to mention the cost of repairs is often hidden behind a low price. I think you're doing the right thing by being cautious and doing a lot of research. In my case, even though I didn't end up with the exact aircraft I thought I wanted, I have ended up with one that will get me in the air "affordably," and leave me with enough budget to fly at a cost competitive with my exploration ground vehicle. Now I gotta spend money on a trailer. And a tailwheel conversion.
