In the last two weeks, I found myself pulling my hair trying to figure out which plane to buy. Am bringing this dilemma to the forum as I imagine many of you wise people have already gone through these debates. Would greatly appreciate your sharing your thinking process, suggestions and solutions. A little background: Mid aged student pilot, no career pilot intention, done with solo, passed the PPL and IFR written exams, waiting for the PPL check-ride. budget $80-120K mission: in the first year or so, this "first plane" is for building experience and skills (not time building) expecting 150-200 hours, annually, in the next fifteen to twenty years (hopefully) mostly myself or with a CFI. I have no plan to take my family with me in the first 250 hours... Don't want to scare them too soon. often destination less than 300nm; must be IFR. need to learn and get my instrument rating. I have zero mechanical experience thus would prefer to minimize the trouble whenever possible. Having said that, I am open to learn and become more comfortable with mechanic stuff So buying a C-150 then upgrading to IFR would allow me to learn and pass IFR. Then sell it in a year or two, and get an upgrade later. This approach has a lower purchasing price, less gas expense, paying a tie-down vs. a hanger; potentially avoiding committing to a wrong but more expensive airplane, as I have limited experience in aviation and have no airplane owner friend. On the other hand, I might miss a better experience flying the “best aircraft one can afford” and/or, get frustrated by the updating avionic process or selling Cessna then buying (upgrading) another plane. If you were in my shoes, what would you go about this buying?