The Rockwood Windjammer and Flagstaff V Lite are "sister" trailers. In other words, they are the same trailer, built with the same materials on the same production line by the same workers. The difference is the name, the decals, the fabric patterns and some of the hardware.
The usual differences are in the options on the unit. Each model has a number of options or option packages available for the same model. There is the standard convenience options...I know, "standard"/"options" = oxymoron...but that is basically the standard model. Then there are diamond packages and emerald packages that change windows to frame less windows, upgrades in hardware, fabrics, laminate counter tops to Corian, and the color of the outside of the trailer (white vs tan). Also, there are options in some of the furniture (small swivel rockers standard vs leather recliners), optional heater (electric fireplace), 15,000 BTU air conditioner (I think it is also a 50 amp electrical service rather than standard 30 amp service) rather than the standard 13,500 BTU air conditioner. Also, some models have standard dinette booths while others have free standing table and chairs, and often those units with the free standing table and chairs also have "atrium" windows in the super slide (tall narrow windows in the slide). There are also packages that include slide toppers (awnings) and a cover to protect the awning when it is closed (on the diamond and emerald packages I think). Also, dealers can carry almost identical units with the only difference being the chairs, or the heater etc. Also, there are differences in the decorations, cherry wood vs hickory (I think) vs mixed woods (light and dark wood combinations) and the patterns of the fabrics, even in the same option level and model .... The difference in price likely reflects a difference in options included on the units.
Look at the units you are considering and see what their options are and which you prefer. The closer dealer may be a better choice due to location, however, it is important to find out the customer service reputation of whatever dealers you are considering. A posting with your approximate location and the names of the dealers you are considering might turn up other Forum members who have had dealings with one or both of those dealerships.
And finally, we have a 2012 V Lite 30WFKSS, the Flagstaff sister trailer to the Windjammer 3008. We LOVE it!!!! It is a GREAT floor plan, and that front kitchen is the BEST!!! I thought I would not like the walk through bathroom, but it is also...the BEST ...a nice large room (full width of the trailer) for dressing and freshening up, and accessible through the front door for rest stops while traveling as well, plenty of room in the bedroom, with privacy because the bathroom is between the "living area" and bedroom. Our unit has just the standard options, which suits us perfectly. There are maybe three options that we would like to have had, but we are more than satisfied with what we have. We started looking in Dec. 2011, thinking it would give us plenty of time to shop around before spring. We were going to enjoy the search as well as hoping to find a unit we both liked. Didn't happen than way. On our first day of the search, at the second dealer, DH decided he wanted to look at the V Lites because he had liked what he had read about them the night before....we walked through the 30WFKSS and I literally fell in LOVE with the layout and everything about it. (I am not much of a "camper" and wasn't even sure I wanted a trailer, especially such a LONG trailer!) We tried looking at a few other units, including two other "great for couples" V Lites, but kept going back to the 30WFKSS. We sat in it alone for awhile, walked through it as if using it, looked it over inside and out....and bought it.
Our maiden voyage was a nine and a half week trip, and we couldn't have been happier with the V Lite. (This is MY idea of camping!) We later took two teenage grandsons with us for a month in Texas...and the floor plan proved to be excellent for company as well!
We did get a better price than we thought we would as we bought off season...winter in the midwest...and rather than ordering the trailer with any preferred options, we bought one which the dealer had on his lot.
Good luck, and let us all know how your search progresses