If you can afford it, you might consider buying your Airstream before you retire, and take short trips every time you get time off from work.
I did exactly that. I bought my Airstream in December 2011, but didn't retire until January 2015. In the three years in between, I took at least 10 trips a year, ranging from 3 days to 9 days in duration. That gave me plenty of time to get used to all of the systems and decide whether Airstreaming really was a suitable retirement lifestyle for me. Every trip was "retirement practice." Then, when I retired and I could devote more time to Airstreaming, I was already past the steep learning curve and I could jump straight to enjoying the experience. In fact, I celebrated my retirement by going to the 2015 Canopener rally less than a week after I retired, going early and staying late just because I finally could set my own schedule.
In New Orleans, there used to be a radio and television personality named Frank Davis. When he was being interviewed one time, the interviewer asked him, "What is the secret to your success?" He answered, three things: one, find something you really enjoy doing; two, do that thing better than anyone else; and three, find someone who will pay you to do it."
I attempted to apply that philosophy when I tried Airstreaming. I found that I really enjoyed doing it during all of my retirement practice. After three years of practice beforehand, I was pretty good at it, though I'd never presume to call myself the best at Airstreaming. And I consider my monthly retirement check as payment to go Airstreaming. So to my mind that makes me both a successful retiree and a successful Airstreamer.
I thought getting old would take longer!