This is something I've been doing since high school. I'm always on Controller.com, playing "airplane buyer", looking for an airplane depending on the bracket of money that I may fit in. I'm normally looking for airplanes priced at or below $35,000.
There have been some deals that I have found online at Controller, and I wish I could be in a good financial position to get one. Something cheap, something to start flying with. I've done it so much, that I have a good idea of where and when to look for a certain plane. I prefer buying a Cessna 150, or a 152 as a first airplane. But, if your mission profile means you must fly with one more, or added range or speed, a Cessna 172 is a good pick. They normally go for less than a comparable Piper (PA-28 family). I prefer Cessnas over Pipers anyway, because of flying characteristics (I've had a couple of really bad landings in a Piper Warrior...she may have been the runt of the fleet, but I was willing to spend a little more on the other planes).
As far as Pipers go, anything in the PA-28 family is good, so long as you can find the deal (which is hard). Since there are so many variants to the PA-28 family, it's hard to find a deal. And because of the cloudy existence of ambiguity, some sellers will take advantage of this and raise their price a tad. But, that's something you need to look for as a buyer.
But, that's just me playing airplane buyer. I'll continue to play the game until the game becomes real in several more years to come. Rather than financing a car, I'll go for an airplane as my first real "big-ticket" purchase.
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