lots to consider - we have talked about getting a toy hauler in the future, and I do already have a low to the ground trailer. Most of our trips are under 300 miles for now, I have considered having the wife pull the bike and me the trailer-just hate going in 2 vehicles .
You can triple tow (trailer behind a trailer) in all the states west of the Appalachians including Maryland but wouldn't work if you live in an eastern seaboard state (although I see people doing it occasionally on I-75 in Fla because thy're coming from states that allow it). Another option if your TT has a twin I-beam frame you could hang a hitch carrier on the back but you'd probably want to keep the weight under 450-500lbs. and invest in a small camera to keep an eye on things.
You need to really do your homework on towing a "recreational double" (ie trailer behind another trailer).
Some states require a special "R" enhanced drivers license to tow a "recreational double". Some states only allow the recreational double if the center trailer is a 5th wheel, different states have total length limits (usually in the neighborhood or 65’ to 75’) , most have a total rear trailer sway rule (my state is nothing over 3” total deviation), some have rear trailer weight restrictions.
Basically if you plan to go multi-state you need to be legal in (& have valid license) for all states traveled through.
I used to haul "recreational double" but it was a real pain-- backing up is about impossible (some jerk would usually find a way to block me in so I would have to back up enough to clear on pull-out), some camp grounds would not allow me in with the double so I would have to drop outside the campground then go back & retrieve it, I had problems pulling into service places without the rear trailer sticking out into a travel lane or blocking a driveway.