It's too bad you're not in the Tucson area. I'd let your DH pull our 36 foot FW down a couple of roads and practice in a parking lot or two. You can get quite comfortable in just a little bit of time. However, it's always good to have reasonable caution.
I've pulled travel trailers in the 22-24 foot range, and fifth wheels from 26-36 feet. They all have their plusses and minuses, but a properly loaded travel trailer with a weight distributing hitch and sway control will do a superb job of eliminating sway. When you look for a new tow vehicle, some of the newer models even have sway control built into the drive train. I've been pulling towable rigs for 35 years, and I've never encountered a dangerous sway situation. As long as your equipment is set up correctly and you load your trailer properly, you'll be fine.
Keep asking questions and we'll all try to help you. Congratulations on your upcoming retirement!
