I need a car under 250 a month that can get me the hill and back....and isnt gay looking

You could probably find a Jeep for that kind of price. My sister got a brand new Cherokee a couple years ago with a bunch of upgrades for like 18 grand after everything.
 
Subaru impreza starts at 200 a month depending on your credit and what not.
I was paying 300 a month for mine with the highest mileage and it was the outback one and i had another 1000 in upgrades and mediocre credit.

You would be surprised what you can get for $250 a month...
 
this is an extremely broad topic haha.

dealer/private?

big name/iittle name dealer?

bank loan/dealer financed?

etc

either way youll need to have full coverage which is going to double if not triple the monthly payment.
 
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