It sounds like you're off to a good start. Take your time and investigate all of your options before diving in. Renting some units is also a great way to figure out what you really need and like. We went to shows and dealers for about 10 years before we finally purchased our travel trailer and it took a lot of time for us to decide what we really wanted.
I also think his concerns with his ability to tow a trailer is normal. I would suggest starting with short local trips on easy roads to get used to towing. Plan the route and make sure there aren't any tricky areas along the way. Find a nice big parking lot to practice maneuvering and work out your role as a spotter. It will take a little time, but he should be OK. This spring I'll be teaching my wife how to tow the trailer and I plan to use the same method.
Good luck with your journey and check back in along the way. There's a lot of good info and helpful people on this forum.
