Rob, Welcome to the Forum and to the Airstream family. Thanks, also for your service to our country. There are many prior servicemen/women here (myself included). The 19' Bambi would, in my view, be better for you due to your height. Check the owners manual for the Wrangler to make sure it has the capacity to pull the max wt of the Bambi. I'm not sure, but you may be close. More experts on the forum will be familiar with the wrangler. The short wheel base concerns me, but I'll defer to someone alot smarter than I am.
Again, Welcome, and thanks for your support.
Fully retired now!
Never start anything before noon and always plan on being finished by 5.
I will never HAVE to be anywhere ever again!