I am also new to this. Our purchase was our first. He was asking 21k, and not IFR cert. The plane looked good. But we hired an independent mechanic to take a look at it and he pronounced it was only an "average" 150.
As I said, the owner spent 4k while it was in annual but we had put a deposit on it, having lost one or two just like you did (to a fast-depositer). So we were anxious to get a plane as the flying season was well under way (this was June of last year).
Well, as I have oft repeated, it took another 6k to get the plane running right, the invariable first year ownership surprises as most will warn you about. Thinking she was a beauty at the time, it was only after the sale was complete that I began to notice all the multitude of hangar rash, scratches, dings, dents, paint chips, etc., etc.
This was NOT the same plane I was looking at when we bought her. The lesson here was, and this is only a suggestion, but bring a non-flying buddy with you whose sole responsibility is to find flaws. We were looking through rose-glasses, giddy with the thought of ownership, and although we did some things right, like letting the seller pay for repairs during annual, using an independent mechanic, and offering him 3k less than asking after all that (which he accepted), we still hadn't seen the trees for the forest.
I think it is helpful to have someone to look it over who has no emotional attachment whatsoever. Finally, I will tell you one thing I am crystal clear on that I learned: if something doesn't seem right, it isn't. Run, don't walk. I learned that if you don't like the sellers attitude, be it in your face or completely flippant about things, there's a very good reason. I learned that many sellers are fully willing to lie to your face to get the sale done. This is truly caveat emptor. I learned too, that when it does feel right, put your money where your mouth is.
Best of luck!