WOW that is quite a list and IMO you have gotten some fairly good spot on answers so far. As you can see I also think you are going to have a VERY HARD time accomplishing what you are looking for and as suggested two things you can do it possibly eliminate this idea is to go to a large RV dealer and look at some of the smaller RVs and second do some research to see if getting a place at a CG near enough to where this option is feasible is even possible on a long term basis. Based on your budget and current TV I would think you are going to be looking at TTs in the under 25' in length range which compounds the problem even more.
Unfortunately I don't think this is going to be feasible or at least without significant compromises.
It might help if you could tell us WHY you want to do something like this to start with.
Larry