Advice needed: what to buy?

I’m in my mid-life crisis years, and I’ve wanted a 911 since high school. I’ve started to look a little closer in recent months, and I feel like my head is spinning with all of the choices. I know everyone has different opinions and that’s great. I’m wondering if someone could maybe help me narrow down what I should be looking for based on my comments here. I just don’t know enough to know if there’s a noticeable difference between 991.1 or 991.2 or 992, or an S vs GTS, etc. I don’t have these at my disposal to drive obviously.

I used to want a first generation 911, but I have a couple of vintage cars already (a Triumph TR6 and an early VW Beetle). I know neither of those are a 911, but my wife also has an Audi A5 convertible and there’s something nice about being able to put the key in and drive with modern conveniences. So I’ve been leaning toward something newer. I kind of want to avoid the new dealer allocation/ADM stuff going on so I’m thinking something used.

I really like the 2014 50th anniversary cars for their homage to the past. I’m not going to track it, not a huge fan of spoilers, etc. So no turbo or GT3.

I’ve only driven a PDK 2018 Carrera T (sweet ride and I was smitten) along with a 718, Macan, and Panamera at a track event - my darling wife won a raffle. So I have no way to really compare. I know some people compare their new 992 GTS with their 997 S and things like that, but that doesn’t really mean anything to me.

I want a nice car to drive around in warmer months. I’m a bit of a purist. I’m leaning toward a cab or Targa. I know newer Targas are all 4GTS, but if cab, I don’t know if I should be looking at S, GTS, 4, etc. As a newbie would I value these differences? Are there any other options I must have if looking at certain generations? I’d like to find something after the fried egg era, although I know there’s value there. But I see big differences in prices between years so I’m just trying to size up what’s worth chasing/paying up for. Or will I just get as much joy out of owning a 2016 S cab as I would a 2022?

I know this is all subjective, but I’m clueless, scatterbrained, and happy to hear any and all thoughts. Thanks everyone.