It's a tough situation because anything with high mileage is going to need repairs at some point. So you have to budget for that. Another thing to consider is the cost of tires. You can probably get a cheap set of tires for the Elantra for $150, but any kind of truck/SUV/Jeep tires worth anything are going to cost at least $75 a pop, and the price only goes up from there. Heck, my '92 Chevy pickup with 15" stock wheels takes 235/75-R15 tires and I'm lucky to find new, brand name tires for $75 each. I could easily spend $140 per tire for the super premium ones.
I can understand your urge to ditch the Elantra. I have always had the feeling that I didn't want to drive a vehicle that I didn't really appreciate. I'd rather drive a beat up Jeep than most of the newer cars I see on the road. Yes, it's nice to have a reliable and efficient ride, but having some personality is always great too. The trick is to find a balance.