Well, I'm quite a lot older than you, but I've been where you've been. I don't care for the "me too" cars, but there are some fun options out there.
Slightly older BMW M3. This car, even as it ages, will be worth something, it's a blast to drive, quite reliable, and no one will NOT consider it a car guy's car. It has a real trunk, and a back seat that's fine for toddlers or kids.
Subaru WRX STi. Very quick car, reliable, trackable, real trunk, back seat that fits adults when required. Resale isn't what an M3 is, but that could work in your favor. Ditch the silly rear wing on the older model and you've got some more stealthy fun.
Honda S2000. Not a lot of money, TONS of fun, dead reliable. I loved mine and curse the day I sold it (to buy a WRX

)
If you move to Boston, the Subaru with it's all wheel drive makes the most sense. All of these cars take modern car seats. All are a lot of fun to drive.
My car progression post college was:
Olds Cutlass (bought from parents)
BMW 3-series
BMW + Range Rover #1
BMW + Range Rover #1 + Range Rover #2 (for GF)
BMW + Range Rover #1 + Range Rover #2 + Camaro (oldest girl)
Range Rover #1 + Range Rover #2 (Both kids tore up cars)
Range Rover #1 + S2000 (left the GF bought a convertible!)
Range Rover #1 + WRX (Current)
Quite honestly, if I was where you're at, I'd get the STi. AWD, can handle a small family, not brutally expensive, reliable. TONS of fun.