Full Disclosure-Total Newbie! Starting "the Plan" :)

Before we retired, we also wondered if RVing would be a fit for us. We started out with a used pop up in decent shape. We spent 2 grand on it and traveled the Southeast for about 2 years on vacation and breaks. That experience sold us.
I wasn't totally comfortable at first backing up a trailer. After practising in a vacant lot for a couple of hours, I felt much more comfortable. Now, it's no big deal.
Good luck.