The OP needs to sort out how he actually intends to use a tractor. If he only intends to use it on his own property, the dealer can deliver it and he doesn't have to have a trailer. The tractor only needs to be sized for his property use case.
If he intends to start doing paid jobs with the tractor that require hauling it, then his insurance company is going to want more money for a trailer endorsement. Then there will be liability insurance issues, and the rest like dealing with customers. Then there are issues like running over T posts, stumps, and other stuff hidden in the brush on someone else's land.
I personally wouldn't want to tow any compact tractor without at least a 3/4 or 1 ton truck, and the weight quickly escalates with the size of the tractor.