The pop-up could be difficult. We are in our late 50's and ours is hassle and we hope to get something else but it is a larger one. Have you considered something like the small Aliner? You might want to look at that and Forest River is making one and they call it a hard-sided pop-up. Something else to look at, which is one of my favorites, is the Leesurelite which is a motorcycle trailer or for very small cars and their website has a video of how it goes up and while a little work, I would think the ease of putting it up and towing it along would make it worth the extra work not to mention the savings on gasoline!