That used enclosed is probably at the bottom of its depreciation, and better for storing stuff, even a car you want to keep indoors.
2 influencing factors might be your tow rig and cost of trailer storage - if you know someone with property, the storage might not be much money.
Seems to me - and I have a very nice open trailer - that enclosed trailers are more highly regarded and better ROI.
Heck, you could rent it out (carefully) and make money off it.
I rented an enclosed to pick up my '69 RR in SD 3 years ago for $100/day.