Do we make the plunge?

Although we owned a pop-up tent trailer years ago when our kids were very little, my husband and I (recently retired) are fast approaching 70. We're both in relatively good health (thank God) but are wondering if we're just too old to start traipsing across the country. I normally do the driving and he's the navigator (he's an admitted terrible driver)! We're also having trouble deciding whether or not to buy another pop-up (for its ease in towing) vs. renting one...or just staying in hotels. If we decide to buy, does anyone have any suggestions (Fleetwood vs. Jayco, etc - they all appear to be pretty much the same) that will comfortably sleep the two of us (he's 6'5" tall)and still have room for our 2 little Maltese pups? The goal here is to drive round trip from California back to Virginia, Boston, New York and all points in between.

Feedback will be GREATLY appreciated.

PS: Would be driving a 2014 Jeep Patriot (hitch & elect. already installed).

Thanks,
Ed & Sharon