Enclosed trailer/toy hauler advice

I have a 20 ft Haulmark that's 20 years old, the paint is shot but the rest of the trailer is in good condition I wish I could find somebody to paint it for a reasonable price. I have a 20ft because that's all I can fit in my driveway and its been fine as I haul my Dart and my D150 in it ( not at the same time! ) I have towed all over the place with no problems except a rear hinge froze and an electric short a few years ago. I have overhead cabinets in the front which really help for storing things , it is a little tight inside with the car , scooter, generator, jack and gas jug etc. but there is still room to move around. A few weeks ago I inquired about a new Hallmark and was told by the dealer they can't guarantee a price and its a year wait.

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On a long weekend race, do you sleep in the trailer or take a hotel.
20 ft is pretty tight.