It's come down to trailer shopping time. Materials are around 2K to build one, or I can buy used for a little more than that and be done with it.
I rented a 20' snowmobile trailer last year to move some building supplies and it was nice not having fenders to deal with, but the added deck height was noticed getting on and off it (I have bad knees). Center of gravity is more of my concern than getting on-off it.
When I hauled the tractor home from SD, I rented a skidsteer trailer, and it had a lower deck height and towed really nice.
Being able to move a 20' container on the trailer would be nice - so another vote for deck-over there. But I'm not sure how many of those I'd be moving besides possibly the one I already have.
I understand a grand or two in the big picture isn't much and I should get a quality trailer before getting too worked up over price. I'm also broke, so getting any money is going to cost me some interest in the short term.
Used deck-over's are few and far in my area, so I'm road tripping if I go used. We have a selection of trailer dealers, so I can work them against themselves if I end up going the new route.
I'll be using this to haul my tractor, with stump grinder, for paying jobs. I'll also use it to move finished lumber, and whole logs, as well as building materials from time to time as I work on the shop/house/outbuildings.
Renting is an option, but it's expensive and I'd be better off with my own trailer.
What to do?