I just bought a 97 Boxster. It was cheap enough that I figure even if it goes to hell quickly I won't be out much other than a lesson. Likewise, if I just can't live with it and sell it quick, I'll get some idea if I'd want a little convertible but not be out much. It has some issues (namely the top and seats both were needing to be replaced, but I lucked on decent deals for OEM replacements). It is currently in process of getting the top swapped over (the plastic window that was on it had deteriorated and so it presented a weather and security issue and since I don't have an enclosed garage and park outside at work, was something that had to be fixed ASAP), so I haven't gotten to properly live with it yet. Seems to be in good shape mechanically (the early years seem to have very low IMS failure rates, but I'm sure something can happen; but I know the blocks in the first couple of years could have issues).
If I do end up liking it, I might think about an LS swap (there's a company that makes a kit but its for the S, but I know a shop that can do all the fabrication themselves, and do it well). The two issues there are emissions testing (which I don't think would be a huge deal but would complicate things a bit) and I'd strongly prefer to keep the auto with paddle shifters for when I wanna play speed racer vs going to a manual. There's a few Boxster engines for sale (think they're newer ones, 2.7L which I believe is the S) which I could have that shop do the IMS conversion on, and rebuild and then I'd have a decent boost without getting too crazy. But even doing either of those I'd still have spent less than $10k total (unless I get bonkers and go for an LS2 or newer).
I'd been considering an Abarth 124 (since with a pretty cheap chip tune can be making 240hp easy). I'd also been looking at the Mercedes SL/K (I'd prefer the SLK really), I like the hardtop and the SLKs "air scarf", but cooled seats on some SLs would be nice too. I checked out some SLs (that were at quite good prices and not too shabby condition but one had aftermarket wheels and and missed out on 3 SLK55 (one was at a very good price at the start of the pandemic). Also was looking at some others. Solstice/Sky, but they were either overpriced or had others issues (and they have like no trunk, which might not be too bad, but I'd like to be able to take a couple of suitcases in case I'd wanna do like a weekend trip to Flagstaff or Vegas or California). I missed out on a Sky Redline that was about the same price as the Boxster (but in very good condition). But the seller was weird (I asked if we could setup a time to check it out and they just responded "yes" and then stopped responding for like 2 weeks and then it was listed as sold). Of course the Miata - they seem to be pretty overpriced in my opinion and I wasn't finding anything reasonably priced. I just missed out on a 2003 C5 Corvette 50th Anniversary model that was about $11k. It was on the high side of what I was willing to spend on a toy so I kinda held off a bit. It was clean, had few mods (lip spoiler on the rear, split air filter intake, and then different but Corvette OEM wheels that honestly were quite nice, they look like black versions of the ZR1 wheels, I forget what model they originally came on). It was one of the few reasonably priced Vettes around. Used prices have gotten a bit silly lately, where I see people listing C5s for $20k (and they're nothing special, not even ZR1s or really low miles or anything). Then this Boxster came along and I checked it out and so figured I'd give it a go.
Personally, I wish Toyota would put a tweaked for performance (engine can rev higher, maybe a li-ion battery pack to save weight, maybe bit higher output electric motor; dual clutch transmission instead of CVT) version of the hybrid drivetrain from the Camry in the 86. It'd differentiate it from the BRZ and Supra, and it should be able to be quite fun (electric torque for instant response), while also having good emissions and unbeatable MPG. Or maybe do that with a new MR2 or Celica. And they could put it in a hot hatch version of the Corolla. If they really pushed it, it could even be shared with Subaru and/or Mazda for WRX/MS3. There was talk that Ford was trying to do that with a new Focus ST/RS.