I think your plans to RV and telecommute full time are possible. But I think your desire to piggy back off someone for 2-6 weeks is not. And I do think if you find someone who is willing to bring you on board for 2-6 weeks will end up very unpleasant and you will will abandon the idea of full time RVing because of it. Life styles are just too incomparable, the way we all do the same thing can be as different as day and night. Do you remember the reality show, "Swapping Wives"??? What happened, in just 2 weeks? There was extreme bitterness between all parties involved. The TV show made it look like, somehow, magically, at the last minute of the last day, they all came together with hugs and kisses and sweetness. Hogwash! That was for TV. Reality is, it was a bad experience for everyone. Unless you are born and raised into someone's life style, you WILL hate the experience! I can't even stand being around my own daughter and her kids for more than a few hours and I'm ready to run for the hills, or if she comes to see me, to send her packing! And she's my daughter! No, your idea of traveling with someone, living in their RV with them, is just not a good thing to do. You may think it is, but it is not.
If you had your own RV (of any type), and traveled with someone with their RV (of any type), in other words, "caravaned" together, it would work better because you'd each have your own "space" and if you wanted to go your separate ways a while, you can.
The only way you can get experience is to do it yourself. Many, many of us on these forums started with tent camping, moved to pop-up campers, and then navigated through travel trailers, to truck campers, to CLASS-C, to MotorHomes ... and then some ... back to travel trailers.
What I'm saying is, YOU are your best teacher. And the only person who can live with you, well ... sorry ... is YOU.
There are several good suggestions above how you can get started. I am of the same opinion you should start simple, local in your area, and on week-ends, or a few days at a time with whatever camping equipment you can wrangle up, if that be a tent, or a rented motor home, it's a start.
If you are 100% convinced you want to do this full time, then go ahead NOW and purchase that RV, but spend the first several weeks taking short mini-trips close to home (like all of us have done when we started out). The time and the distance eventually get's longer and longer. You learn something every trip out, you come home and have a chance to re-group, recover, re-think, re-focus, and re-plan for the next trip out so you can improve or fix the mistakes you encountered. Eventually YOU will have the confidence, the knowledge, the experience, and have all the tools needed to hit the road permanently. THERE ARE NO SHORT CUTS, THERE ARE NO SUBSTITUTES to self-experience.
This is my recommendation. Purchase the RV and start taking small trips. It starts by camping in your own drive way the first few night! If you don't have a drive way, you go camping at a very close by campground so you can get home, or have access to the closest WalMart for things you've forgotten.
I'm not trying to be "downer" here, but speaking from experience, you really need to do this yourself, on your turf, on your dime, with your own ingenuity.
YouTube.com is chocked full of "how to" videos for everything imaginable when it comes to every kind of RV and every kind of camping topic. YouTube is a great teacher. I've used it many times myself. This is the best advise I can give you.
