Although we've moved on/up (depending on how you want to look at it!) we did have a Rockwood 10' box Pup for 3 years. My pro's/con's are similar to everyone else's.
Pro's: lightweight, could be pulled EASILY by my Honda CRV, great gas mileage, could have stored in my garage (if there had been room-LOL!), could move it by hand so I didn't have to bother with 'backing up', easy maintenance, no trailer brakes or WHD needed, what I could afford (bought it 4 years old & paid $3500 cash), held value well (sold it 3years later for $3200 in 2 days!), got us up off the ground & with some amenities (better than a tent). Also LOTS of room when opened up & could sleep a number of ppl.
Con's: the major one is we did 90% of our camping during the summer in TX, FL, & AR. Unless we got a site COMPLETELY in the shade, the 13.5 BTU AC couldn't keep up. Even with a tarp over the site AND covers over the bunk ends. And putting up all that extra 'stuff' just to keep it in the 80's got old after awhile. FORGET overnight camping. Just wasn't worth the set-up in the summer.
Other Cons: set-up/take down, leveling so the door would fit right, minuscule 'fridge' if you want to call it that -- that required also being perfectly level, added cooling fans to the back, and BARELY kept things cool in the summer. Lots of movement even when leveled, blocked & chocked. No permanent storage & had to open it up to access things & load/unload it for every trip. Awning was a pain to set up & stake down.
And the other major thing that finally caused me to then buy an HTT: the wind effect. The Pup never leaked (& we were in some pretty amazing storms!), but OMG the wind causing it to move scared the Beejeebers out of me. Once camping at Ft. Davis in Texas at night, the wind was gusting 35-40 mph and shaking the Pup so bad I made DS get up and we went and slept in the CRV. I was THAT scared it was going to tip/blow over or the roof was going to come off. It didn't of course, but it was scary! We had several other instances where the wind & the Pup's shaking/moving kept me up all night. So that was basically 'it' for me.
However we did make some awesome memories in that Pup & I've never been sorry I bought it!