OP, keeping the house is going to use up a fair amount of the $5500 after tax dollars unless you rent it out... Likely a area of new problems. Unless you are willing to get rid of the majority of your stuff, including the home... maybe you should start out as half timers. At home Spring and Fall in NC, Winter South and Summer West. This is what we do as there is no way I could get rid of all of my stuff plus the grandkids are here... Happy wife.....
Does not sound like you have a Roth IRA so cashing in your retirement will be expensive increasing the real cost of a new truck and trailer. I would suggest keeping what you have and start out as half timers and see how it goes. After a couple years you will have a better idea of what will work for you and the DW.
* OP, In reading your posts I get the feeling that like me you are hands on. Without a home base of operations it will be hard to fix things yourself. Being at the mercy of someone else fixing things would drive me up the wall.