For 1500-2000 price you may find yourself paying in for fixing up the trailer. Tires, breaks, lights, flooring, etc... go out over time and you could run into that problem if they arent taken care of.
I hate my stcok trailer that I have now, I could get $2000 on a trade-in but I don't think I want to pick up another payment at this point in my life, and it gets be where I need to go. Over the last few years I had to put in new flooring (my dad and I did it), lights, and bought new tires last spring (spendy), but the trailer is sound. It needs new paint but it is going to cost more then what it is worth.
Basically what im saying is you get what you pay for, usually cheaper the trailer more money you are going to put into it.
It's not the will to win, but the will to prepare to win that makes the difference.
- Paul "Bear" Bryant (Former college football coach)