Boring vs Fun Daily Driver?

[FormulaDz92]

Hey guys and presumably some gals. My question to you all is given your vast car experience, is it better to have a fun daily driver which will cost more up front, cost more to maintain, require more maintenance and therefore take money away from my '89 S13 Hatch OR a boring daily and save money across the board and also make the Nissan feel more 'special'. What sort of dailys have you had? Did you regret any them?

Possible Fun Dailys: 2003-2006 WRX, Forester XT or Mazdaspeed 3

Possibly Boring Dailys: 2000-2007 Impreza/Forester/Legacy/Outback or Mazda3


Contributing Factors:

-Budget: 8k max
-Area: NYC's NJ Suburbs
-Age: 24 (so not much money but finances improving)
-Past DDs: (all very slow) '98 Volvo 850 Wagon, '97 Mitsu Eclipse N/T, '05 Honda Civic EX Coupe, '89 Nissan 240sx, '94 Jeep Cherokee XJ (Current)
-Body Style: Anything easy to load unload Hatchback, Wagon, Small SUVs even small Pickups. Basically no sedans.
-Gas Milage: Just nothing worse than my lifted Jeep Cherokee's Measured 21 MPG average.
-Manual or die.
-Not RWD (all other cars in the family are RWD)
-Must be pre 2008. I don't want too much refinement... I don't like feeling isolated in the cabin.
-I like my XJ but will probably stay away from Trucks/Jeeps due to handling

Thanks!

*If there is another thread out there like this I apologize. I tried searching.