What is the right first car?

I'm shopping for a car. I'm wanting a SUV or truck that is under $15,000 and under 80k miles. I need to be able to pull small trailers, haul friends around, and be reliable enough to last throughout college (which I will start in 2 years). I also prefer it is a 2008 or newer model. So far I have the Ford Escape in mind. Are there other make and models I should consider?

P.S. I like the design of the escape. It is very spacious with a good body look to it. Very 'guyish. I just don't want a 'chick' car in other words.

IPod Touch not working in 2010 Ford Escape?

I have had this car since 2011 when my parents passed it down to me after graduation and have always used the Sync player/USB for my iPod Touch. It was fine until I lost the original iPod cord (the type you squeeze the sides and it disconnects from the USB/charging port) so I don't know if that has something to do with it?

Right now I just have a cheap iPod cable I bought from the store and it works fine to charge, but my vehicle does not recognize anything is connected to the USB port. I've checked online for any Sync updates, and everything says I'm fully updated and I've checked fuses, and they all seem fine.

I did try the iPod on my parent's car and it did the same thing and their SUV is much newer than mine. Does anyone know what I can do to fix this?

How much will this car depreciate?

So, I want to buy a 2004 Ford Escape XLT at $2500 which I could, but if it costs that much right now how much will it cost next year? $2300? I'm currently driving my step dads side car which is a 2004 Honda Accord… If I wait the price will go down, insurance will go down (i'm 16), and I will have more money and could possibly purchase a newer model… What should I do?

Added (1). I also have a part time job that I make about $2400 every month…