Matt,
Since we have met, and I was impressed with your outlook on life, I have given your car plight, replete with your acknowledged automobile ADD, some thought.
Let's review:
- Young man, beautiful wife and kids. Check.
- Worked your way through college (very cool). Check.
- Future is bright. Check.
- Has 5k in cash to spend. Check.
- Needs a DD that won't crater his budget. Check.
- Car has got to be, "interesting". Check (and the kid could be my son

)
What to do?
I'd get a pre-owned certified Honda or like car, pay around 16k. No worries, no dicking around and the A/C will blow like a nor'easter.
So, the payment would be, after 1k down and 60 months, $300.00 a month. That gives you, assuming the 5k is liquid, over a year of trouble free, cost free driving covered by the pre-owned warranty. Since you're a smart guy, I'm thinking next years raise will cover the nut
Then, assume any of the more exotic used car excursions your are pondering and have paid cash for hick-ups at all. My low end guess is to think $1500 to $3000 out of pocket! Ouch. That is for one burp.
That little budget wave would have given you another year of trouble and risk free driving. And the A/C is still frigid.
Look here:
http://www.shonda.com/
You can be stupid with cars later. You need a DD.