I'd suggest holding off on the full-timing for a bit, and instead just get an RV to take trips with. You can start with shorter trips while you get familiar with the systems, etc. This will also give you time to get your dog acclimated to RV life. Then extend the trips out as you feel comfortable.
Since you telecommute, doing this wouldn't be a problem. You could get the ins and outs of your internet issues. Start by seeing the world closer around you and then move out as you go.
And if you buy a used/ex-rental smaller Class C (24ft), you wouldn't have to worry about towing a car. With a dog that size, you could easily toss in a bicycle with a basket for trips into town, etc.
Since you indicate you're keeping your condo, then why commit to full-timing immediately - take your time and get used to it first. And with the condo, it's not like you will have to take everything with you, so the smaller Class C would probably work just great.
As for the idea of going with a stranger for 2-6 weeks, my issue with that is a bit different. I don't think the person is necessarily going to kill you, but I think spending that much time in that tight of quarters is difficult. It's not like a hotel room or cruise ship where you can just go off and do your own thing. When you're driving for the day, you're STUCK in that small space with that person.
And there are lots of little idiosyncrasies that you don't learn about people from a background check - the 3 hour daily naps (when you are unable to move about the RV), the over-friendliness (inviting everyone into your space when you just want some time alone), the constant moving (please, just SIT STILL FOR 10 MINUTES!), and so on (and that could be about you or them).
While you indicate that if it goes "bad", it's just a quick trip to the nearest airport, that airport could be hours away and in a different direction than the other person is headed. Creating more hostility and antagonism in an already negative experience.
