Because you're used to tent camping, I doubt that a pop-up is too much work. While I haven't owned one, I have to believe that it's easier than a tent to setup and more comfortable.
The other advantage of the pop-up is that it's easier to tow with less strain on you and the tow vehicle. It's more compact and some can even be stored in the garage when not in use.
Since your vehicle has a low tow rating, I would be inclined to stay the pop-up route. Jayco has the "Sport Hard Wall" series which may be an attractive route as it appears to be really easy to setup and would probably be a good candidate for a rest area / Walmart stopover.
You can download a brochure
and take a look at the various options. I would personally shy away from a travel trailer because with a 3500# weight rating even the smallest travel trailer is going to be right close to that rating and could be difficult to tow.
As a final note.... I have seen more women (single moms and 2 women pairs) in popup's than in smaller trailers.