John, if you're still pondering which Porsche you might like best, and are fortunate enough that cost isn't "the" most significant impediment to owning what you really want, I oh-so-humbly recommend you drive a few. I realize that may sound trite, and that it may be somewhat difficult to do, but the various models -- 356, 911, 993, etc. -- really are as different as chalk and cheese.
Owning Porsches -- particularly used Porsches -- wasn't all that expensive when I was in my '20s. I started off with a 1958 Speedster (in 1970) that the then-current owner had worked at bringing up to snuff, and I thoroughly enjoyed it -- meaning I drove it like a car, not a museum piece. (Chassis # 84190, if anyone happens to know where it is now). These days people pay a fortune for them, which I think is hilarious. (I'd tell you what I paid for mine, but no one believes me.) They are fun to drive, but I can't imagine paying multi hundreds of thousands for one. In 1971 (I think) Car and Driver p#$$ed off the world of Porsche owners no end by comparing one with the then-in-production VW-Dub Karmann-Ghia. The Ghia came out on top. As it happened, I owed both at the time, and I knew C&D was correct. (Indeed, those who have re-built various 356 components learned early on that a lot of 356 parts were, if fact, manufactured by Volkswagen AG, and that Porsche simply re-stamped the part numbers. At the time, you could save a lot of money knowing that.)
Next up for me was a 1994 RS America. Lots of character. Fast. Strong. I bought it from a young gentleman who thought he wanted a Porsche RS and realized shortly thereafter (within 600 miles of ownership) that he didn't. I'd had the opportunity to drive one before I went hunting for mine, so I knew the street ride could be, well, brutal. But it was strong runner with a lot of genuine Porsche character.
Next up, my favorite Porsche by far: a 1988 911 Club Sport. I bought this one "used" also, but it was barely used. The owner was a very wealthy man who had a unique collection of early Porsches and Porsche race cars, and the Club Sport (one of 21 1988s) just sort of sat around for 10 years when he put an add it AutoWeek offering it for -- get this: $36k. I flew to Chicago, saw it and drove it. But it really didn't impress me that much initially. Months later, on a hunch, I called and asked if the owner would take $32k for it. He did. It turned out to be a wonderful car. I drove it for about a year strictly as a "pleasure car" on weekends. Nothing stupid or racing around. Just enjoyed it. I've owned other Porsches since then, but the character and feel of the water-cooled cars is completely different from the 356 and 911s. And understandably so. The automotive world has moved on. But IMHO, the 911s of the late '80s are special. If you can find one that hasn't been messed with too much, were I you, I'd start there.
Oh, let me add "my" Club Sport is now in the hands of a Texas dealer. It now has approximately 6000 miles on the odo. (Chassis # WPOAB0919JS125076.) You can google it. You will have to call for the price. I recommend you be seated at the time.