Hi Corey! I wish I could offer you some advice on buying but I am a renter and as with all renters I hope to be an owner some day. I learn more and more every time I log into this club. The resources here are great. There are some good past posts on buying. One in particular was about 7 pages long. It started just about the way yours did and went on and on about different planes and different opinions. But the end result had a happy ending and the fellow purchased a plane that was in his cash market and I believe he is still very happy with it.
As far as a CFI, Pro's and Cons on both! I guess you will get many opinions. Mine for all it is worth is, a smaller airport and a fellow who enjoys to instruct. Because your not paying for all that taxi time that you will get at a larger airport, and when you go to a corp. school most CFI's meters start running the moment you say good morning to the moment you say good bye. The CFI I had to get me current again was a guy who had his own 150 and instructed for the joy of instructing. I only paid for the Hobbs. Rare? probably, but they are out there. Good luck on your shopping! Hope to see you at Clinton next year showing off your plane!---TIM