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Similar question: I'm looking at enclosed trailers and while a 20' is plenty for a spec racer or other car and some gear, I'm wondering if I want to spend a tiny bit more for a 24' so I could maybe haul two of them if needed. It seems like it's a common enough size that it really isn't much more to spend but I'm worried that slippery slope would take me up to 26' or bigger to carry two spec racers and a bunch of associated gear. Just trying to avoid realizing I actually needed more.

I had a 24ft. steel trailer and 2 spec racers just fit in.
You must put them in nose to tail so you don't have much choice on weight distribution. I put in racks with e-track to haul parts and tires over the cars. I got a toolbox that just fit in the back of my Avalanche. I needed an anti-sway load leveling hitch.
I replaced the steel trailer with a 26ft. aluminum one which allows for much more storage and pulls better. I got a great price by watching craigslist for months before the right trailer came up. And I found you have to be ready immediately to close the deal. The 26ft. trailer is much lighter than the 24ft steel one.
Elliott