I've had my 993 since 2003/2004- at that time it was one model series old, the 996 was at the end of it's run and the 997 hadn't come out yet. For about 8 years the car was a daily driver and never had an issue using it as such, I suppose I was just used to it, I still have the car now, but over the same period I've also bought and used other cars in parallel, but the 993 is a car I just could never let go of.
I've had 8 series', fast jap cars (300zx TT), SLK 230k, Infiniti SUV and a couple of S classes, all of which were in fine fettle as I'm very particular about the condition of each of my cars... all these other cars came and went but the 993 stayed...
Every time I get into the 993 I look at the stark old school dash and realise (and appreciate) that when it comes to the enjoyment of driving itself, it has literally everything you need - centre mounted rev counter, great soundtrack, no mod cons to distract you, and the bluetooth in my Becker Indianapolis Pro is as much as I need. Everything is about the drive itself - the visceral experience and enjoyment which has never waned since buying the car.
In terms of comparing with newer cars, my dad and brother being in the trade has meant that I've driven almost all variants of 996, 997 and 991.1 (carreras and turbos rather than RS/GT type cars), and I often drive my brothers 996 TT, and my dad's 996 C2, and for me, while they are all no doubt objectively better, they all somehow feel related (not driven the new carrera turbos mind you) - difficult to put the finger on why exactly that is - for example a nissan GTR no matter how good definitely doesn't feel related; so there's something in the DNA. I never feel short changed when going back in my 993. And personally the offset pedals and quirks dont bother me - but I also use an S class as a daily so I get my modern relaxed luxo barge fix there, however the 993 is always an event to drive. My 993 also goes out in all weather - snow, rain whatever.
Bit of a ramble for sure - best thing is to drive one and see how you feel, you may not like it!!