I totally agree that a high end brand will hold it's resale value and in the long run "cost less" than a cheaply built trailer.
I also think there is a price to be paid for "pride of ownership". I always liked it when I was on the road and some trucker would tell me how nice my rig looked . I just don't think that if you're on a budget... and don't really use the trailer for many events or many miles per event... that it needs to be fancy or aluminum. It just needs to be well maintained (think brakes - bearings - tires/wheels) = and doesn't leak. And frankly -- if you're only doing 3 or 4 events per year -- and maybe 1000 mile round trips... it could be a pretty lightweight (as in build) trailer.
Tires on a lot of used stuff may need to be replaced -- they might have plenty of tread -- but be sun rotted --- or just flat OLD.... and the first thing I'd do on any used trailer is all the wheel bearings... which is something most people NEVER service... and they should be serviced annually.
The brakes on these are generally electric.... and are activated by an electro magnet. This is something else that needs to be serviced because of a LACK of use.... they get rusted up and stuck etc.
So by the time you put 4 new tires on -- service the bearings and brakes... you've just spent another $500.
You can buy a BRAND NEW 24' enclosed car hauler -- for less than $5K. For the amount you stated you would use it... how could you go wrong?
http://www.ebay.com/itm/8-5X24-ENCLO...item2ec893c97f