Boobdocking...Certainly got my attention! In answer to the intended question,I would,and did choose a 5er over a class A.
Maintenance costs,higher on a motorhome than the fiver and TV.Insurance on two motor vehicles,If the truck breaks down,you still have a place to stay while repairs are made. Many more places to have repair done on a truck than a motorhome.
There are those that feel a motorhome is the best way to go and you will hear from them also. There are pros and cons either way,bottom line,it will be up to you to decide after the homework is done.
Whatever you decide...Enjoy your new lifestyle!
(BTW,you may get more response from the folks at the Full timer section of this forum.)