We bypassed all the other stuff & went straight to a 34' 5er. It was our first experience with towing anything EVER. Learning to drive it was no big deal. I had done a basic police driving course just for the fun of it.
Going from a car to a 55'LOA crewcab longbed dually & trailer took time, care & being aware of my size & weight.
As far as the RV maintenance went we had the advantage of over 20 years of boat ownership & the much more complex but similar systems that a cruising boat has.
Overall it was a very easy switch. Nothing to be aprehensive about.