It's like buying a car, you get a deal you feel OK with, go for it. If it's more than you're willing to pay, don't buy it. (If I worried that much about getting screwed, I'd never buy anything!)
We bought a 2012 Roo19 in April, Milwaukee, WI; paid $16,725. Seagrass interior. I think the cabinents are Tuscan (maybe Hickory, I don't recall). Came with the "Convience Package" (13,500 BTU A/C, 22" LCD TV, TV Antenna, Microwave, 6 gal gas/elec wtr htr, awning, windows w/ tinted safety glass, outside speakers). Also has the outdoor grill, which works very well. Have been out about 8 nights, one VERY heavy rain, a couple normal rains. We've only used the front bunk at this point, but no leaks. Somewhere on this forum someone who just bought a 2013 Roo said he got LED's instead of incandecent lights for the interior; I'm sure that ups the price a bit (ever priced an LED?). Have been happy so far. Biggest gripe is the folding table. To heavy and hard to fold/unfold.
One comment regarding your past life with a popup: I pulled a 1988 Coleman Sequoia for 20 yrs with 3 different Dodge Caravans. No problems. Now I'm pulling the Roo with a 2011 Chevy Traverse. Not happy. Traverse tow limit is 5200 lbs, and I'm probably not over 4400 lbs, but the problem is the drag, not the weight. Didn't expect drag to be the problem it's become. Runs in 4th gear on level ground, 3000 rpm, 10 mpg. I'll probably look into a used V8 pickup with a little more umphh for a tow vehicle in the spring.