My first instinct is to tell you to drive one first, before committing. They are amazing, but not everyone enjoys the weight distribution (I know, some folks are weird!) and it took me a year to get used to it properly.
Outside of that, do you want 2WD or 4WD? My initial thoughts would be a 991.1 GTS, as you get the NA engine which is beautiful, plus as a GTS it’ll hold it’s value. The flip side would be the interior isn’t as modern as the current ones, which would certainly be in budget. At the mileage you’re looking at you can certainly expect some depreciation, but it depends on how much mileage you’re intending to put on it.
The 991.2 and 992 are both fabulous turbo cars, and are ridiculously quick. Spec will be dependant on previous owner obviously, but I’d consider the 18 way adjustable seats an absolute must have. The other comfort stuff is down to individual taste, but do get the sports exhaust. The PDCC makes the car feel very nimble along with the rear wheel steering, however you do lose the traditional 911 feeling. I couldn’t decide whether I’d buy with or without tbh, and still can’t. Probably without and enjoy that fabulous chassis a bit better, and do the driving myself.
I’ve loads more info if you need, see if you can find some examples of cars on PH or wherever and post them up and I’ll see if I can give you any more hints.