All good advice. And yes a 30' trailer is a lot of trailer for someone who's never towed or is inexperienced. That said, it's not horribly difficult to tow and back a trailer.
The length don't mean much when towing down the road, it when you get into tight quarters of as mentioned, don't fit somewhere you want to camp. Idk how often that happens though. Not a campsite expert.
I do tend to forget the challenges learning to tow and back a trailer since its second nature now.
If you are reasonably adept at spatial and mechanical concepts then I'd suggest taking the New trailer by yourself for a couple practice runs. Do city, highway, practice backing, etc.
I think you'll find it's not terribly difficult. Just requires more attention than driving around bobtail.
The 2 car thing isn't a bad idea, mainly to remove distractions..... The kids!
Fun to stick the wife with them lol and trust me much easier to think about what you're doing.
I've been towing all kinds of trailers since I was 15 and 25 years later I will get distracted by the kids and yell at them. They don't seem to notice when you're heading up the pass, in snow, trying to change lanes, back into a driveway etc.