Alright, so I'm back to waffling on this topic. I've spotted two alternate cars that are luring me in.
1) A 2004 Boxster SE550 for a very reasonable price (under $20k, manual transmission with 110k miles and one owner).
2) A very nice 993 Cabriolet (under $40k, 40k miles and several meticulous owners).
Option 1 appeals because I could probably sell off my '99 and all my extras (hard top, extra wheels, short shifter, etc.) to cover the majority of the cost. I'd gain over 60hp and all the improvements over the course of the 986 evolution. My factory car cover, roof transport system, and speedster humps would still fit it too. (So would the hard top, but I'd doubt I'd ever use it with a glass window soft top.) The SE would also hold is value more than my current Boxster would.
Option 2 appeals because the car is just so sexy. My dad had a silver 993 back in the day, and I've been pissed with him for years now for selling it rather than gifting it to me.

The silver exterior and red interior just looks so great on a Porsche too. This 993 cab has low mileage, upgraded litronics, a new soft top, and appears to be impecable condition. It will hold its value or appreciate well. And those rear seats might prove useful one-day (briefly).
Option 2 would require $20,000 more. I'd have to finance it for sure. I'd probably finance Option 1 too, just so I wont feel pressured to sell my current Boxster too quickly and too cheaply. Either vehicle would require a quick plane flight to the seller and a scenic, coastal roadtrip home.
Thoughts? Fatmike, you made the 986 to 993 transition. Any regrets? I realize these models are a bit of an apples to oranges comparison.
As stated before, I primarily use my Boxster as a daily driver and for weekend get-a-ways and road trips. I haven't gotten sucked into the AX/DE world somehow...yet. I'm not opposed to picking up a cheap beater for my daily driving (like an e30 BMW), if I wind-up with an 'investment' car like the 993.