I am 36, have been RVing part time since I was 27. I spend about 6? months a year in my RV and work from the RV/home as an IT consultant for a fairly large tech company.
I have a wife and 1yr old child, before the child I had two dogs. Working from the RV is fine, although i am required to be on conference calls I have a 38ft fifth wheel that allows me the space and silence to complete. I do have a freind who camps mostly where we do and make use of their camper as my office when available. I have found Wifi at most campgrounds unreliable, the better spots seem to be further away and have less connectivity, asking at check in can often put you in a better wifi location. As peak times approach it gets worse, steaming Netflix for me rarely works and for their reasons installed a wind guard satellite system and pay for a subscription. I also have a cell plan that gives my wife 3gigs a months nd I 3gigs a month, which for work purpose and general browsing is more then enough, I use on average 2gigs a month.
I have not jumped full time, although I would love to, like having a place to call home, a base so to speak. I see no real holes in your plan, a motorcycle will do the trick but a smart car used would be around the same money and give you the added freedom of not caring about the weather.
Good luck and enjoy, your 27, I had a father who past away 6 months before retirement with cancer, he told me before he past not to wait to do what I want to do, I may never have the chance.