Some good responses already. Just sharing my experience:

After many years of owning 911s starting with longhoods and successive newer versions afterwards, I started going backwards when 991s came out. Some were dailies and some were track/race cars.

The first backwards move was a 3.2. In fact, I tried to daily a 3.2 twice. An 86 for 10 months and an 89 for 2 months. Lackluster AC, no power steering, faint oil smell inside cabin, heavy feel - all endearing with mechanical noises when driving for the sake of driving but not when daily driving and fighting traffic.

I then considered a 964 - my favorite street air cooled 911 to own/drive; I dailied one for 4 seasons in the midwest back in the 90s. As part of my backwards journey, I borrowed my brother’s 964 a few years ago for a couple of days to get a feel for driving it on a daily basis. Nope, didn’t work.

Afterwards, I test-drove and eventually skipped the 993. Those never felt like the traditional air-cooled 911 to me, which is a bummer as I still like its aesthetics.

This may not be popular in this 911 forum, but the Goldilocks daily 911 for me turned out to be the 996, which I first daily drove in the 00s. Since beginning of 2018, I’ve been daily driving a 996TT and still loving it. For the budget you have in mind, the 996TT with the GT1-derived Mezger engine is a lot of car especially for the money.

Nowadays, I’d only own an air-cooled for vintage racing/rallying. I’m hoping/waiting for market to further settle down on historic race early 911s.

Everyone has his/her own journey.

A C4 964 coupe is also possible in your budget. Certainly an early one, but those have the engine leak issue. I am a big cab fan so I am happy they are worth less money than coupes. None of these cars are all that fast so give one (or a Targa) a shot on a test drive. A lot of nice cabs used as cruiser whereas a lot of coupes have been beat on, tracked, and modified so harder to find a nice one.

993 never really dropped all that much in value and the run up was not as steep like C2 964 and long hoods, but the cohort of people who admired 993 as kids are not quite old enough to be in peak buying age. Hard to see that much downside on a 993 coupe, but worrying about value is a fools errand.

I was in your shoes a couple years ago and got a high miles 993 C4 cab that was in really nice shape (no joke, woman owner for most of its life, then a doctor who drove it sparingly). Other than eating a couple alternator belts and a few basic cosmetic things I fixed because they bothered me (chipped headlight, floormats, shifter, steering wheel, engine pad trapper thing) I have not had any issues or costs beyond a service. Never really looked for a coupe and was not looking for a C4, but when I saw it, I did not mind the fact it was AWD. Now I actually really like it as it makes it safer in my view to have all four gripping.

Can’t go wrong with your choices, so I would buy the best car you can find/afford as that makes all the difference. Especially if you want to drive it a lot.

Aged leather. That’s the good odor.

The faint oil smell is most prevalent for me when starting the engine with heater on; it’s largely mitigated when ensuring heater is off and turning it on when already moving.