I work from home and my wife works about a mile away from our house.
Please tell me she walks or bikes... 1-mile trips are awful for a car.
We also visit family once a week who live about 20 miles away and go visit her family every other month. They live a few hundred miles away. We do drive over a mountain pass, but we only have to worry about poor conditions twice a year.
Snow tires for your car should be very cheap - Tire Rack will happily sell you a set of wheels and tires you can swap out yourself. Blizzaks or something on a FWD car will give you enough traction that if you can't get through, the road was probably closed an hour or two ago. Or you're being stupid on purpose. ;) Yes, you can get a Subaru with snow tires stuck somewhere.
...especially because we'll be heading over the pass for Thanksgiving and conditions aren't looking stellar.
Unless I'm badly mistaken, the Fit is FWD only - there's no AWD version. So it wouldn't be any different in terms of driving in questionable conditions. Snow tires are a better investment. It's probably too late to order a set from Tire Rack, but check your local tire shops and see if they've got anything, if you're worried about conditions.
I'm torn, because it would be nice to have a car with a working clock and radio, but I know I don't really need it.
So... fix the clock and radio. A new radio isn't several thousand dollars.
Lastly, we have a 5 week old baby, so I'm also worried about safety, but recognize that it isn't a dramatic difference between my Altima and the Honda Fit.
Correct. Put the car seat in the center rear and don't worry about it. There's not a huge difference, and it's not like you're carting the baby to day care every day during rush hour, right?
So, my question is, has anyone given into the temptation and upgraded for a few thousand extra and if so, do you regret it?
We upgraded from a Mazda 2 to a Mazda 3 for more than few thousand, but I didn't care for the Mazda 2, the stroller didn't fit, and we wanted a nicer car before we moved somewhere with lower income - I expect to keep it for another 20+ years.
Certainly not the wisest decision financially, but it was in preparation for a move to radically reduce our cost of living.
So, uh, do as I suggest, not as I did? :)
1) Increased MPG
Do the math. That won't pay for the cost delta in a reasonable time, given how little you drive.
2) Safer care for winter travel with our new baby
Snow. Tires. Huge difference. It's not like you're talking about getting a Subaru or something, and even then, you still want snow tires if you're going through snow.
3) Fancy, albeit unneeded, features (clock, radio, speakers).
$200 if you do it yourself, probably $400 if you let a local car audio shop do the work, and you can have all of that in your current car - even with bluetooth! My truck is 20 years old and has a perfectly nice bluetooth stereo in it (it could have a reverse cam as well, I just haven't bothered buying one and wiring it in).
I'd also be tempted to finance, not because I can't afford to purchase outright, but because I can average much better returns investing over the interest rates I'd be looking at.
What kind of interest rates are you getting on a used car that you can beat investing?
I'm not gonna lie, I feel like this would be a total "want" decision, not really based out of necessity. And I have absolutely no reason to believe that my current car is unreliable or unsafe, beyond it's ability to make it through the pass in the winter. I'm just trying to gauge whether I spend the money now for present happiness and have to work an additional 2 months before retiring and if that would be worth it. My current savings rate is about 60% before tax.
I mean... if you want the car, get the car. It sounds like you're on a perfectly good path.
But nothing you've stated as a problem with your current car requires a new car to resolve, and a Fit will be just as bad in the snow as your car if you don't put snow tires on it.