Regarding the move to earlier Porsches from replica speedsters, I've owned dozens of air and water cooled 911s. Strating with a 1970 911s, moving throught the late 70 SCs, late 80's Carreras, a factory 505 slantnose 930, a 96 993 TT, and a number of 996s including a 996 X50 turbo. I also crossed over and experienced the Ferrari life for a year through a 98 355 triple black F1 spider.
Eventually, I've gravitated to the simplicity of the replica speedster. Pure and simple, it delivers a driving experience that is removed from any of these other cars in terms of being unconnected to any modern car, and more connected to the simple experience of driving (some have mentioned its like a 4 wheel motorcycle). That's what I was ultimately looking for, a driving experience each and every time I drove the car that I couldn't associate with my daily driver Audi S4. In fact, I get that experience from the moment I sit in the car and turn the key.
Further, this is a driving/ownership experience that does not freak me out putting miles on the car and/or dreading breakdowns, or even worse unknown dealer repair expenses (figure about 10 percent per year of the purchase price of a Ferrari). This is a car that you don't have to freak out about where you park it, and nothing on the car that breaks or wears out will break the bank.
For $20k or less you can have it all. For those moving away from the speedster replica experience, its probably based on the individual and their desire to seek a new experience, which is human. Believe me, I have tried to talk many friends out of buying a Ferrari (by sharing my Ferrari ownership experience) but couldn't, and I understood it completely. And after my friends all evantually sold their trophey car we both laughed at the experience and weight that had been lifted the moment they sold the car.
So in summary, I would say just buy what you want and seek the experience you feel your current car is not capable of delivering and that you feel you are missing. However, this requires that you take the affirmative step and seek the experience, and not be paralized by analysis. Be a participant! Live! Then critique from perspective.