An enclosed is great, but it will certainly not be very easy on the truck with the wind catch and all. Where we live I'd recommend more towards the open trailer for the hills, etc. I have an open trailer now with a front nose and use almost 9ft ramps on a dove tail trailer to avoid loading/unloading damage. If I were to pick up another open trailer it would be the SUNDOWNER -ULTRA (22'ft) and I believe they come with 8' ramps and have a lower deck height than some. Hope this helps.
http://www.sundownertrailer.com/tlr-ULTRA.html