I tow a
TrailManor 2417 Sport with a 2007 Grand Cherokee diesel. No problems. Dry wt 2350#, camping weight 3300 lbs (weighed fully-loaded). 17' tow length, and I can get it turned around in some narrow off-road locations.
But, if you don't want a hard-side expandable, then a canvas pop-up would be the way to go. Since the beds pull-out from the ends (just like the TrailManor does), you have more floor space than a model that doesn't expand. We had a canvas pop-up for 10 years before getting the TrailManor. Love the TM, but pop-ups are a great first step into trailering, especially for your type of use.
Don't know of any trailer with a built-in genny, though. You will have to haul that separately.