I purchased my -84 targa 9 years ago with 58k miles. It needed a new alternator and battery pretty much the next day. Luckily the local imports dealer didn't leave me hangin' on that deal. I did a lot of research before buying the car and had the dealer do a valve adjustment and oil change prior to my purchase.
My car has really been trouble free. 90% of the ownership costs have been parts upgrades and other issues I chose to address. The had the car repainted 2 years ago and the clutch just got replaced at 95k. Regular maintenance has consisted of valve adjustments every 15k and oil/filter every 3-5k. 911s are fun and relatively easy to tinker with too if you have some time.
The bottom line is try to find the newest 911 you can afford with as many tasteful performance upgrades as possible.
I would guess a working a/c system would be an asset in a daily driver around where you live.
jt
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