I believe the Shadow Cruiser and Fun Funfinder are pretty much identical as far as the floor plans go. The FF is a bit more 'plush' with some add ons like the front window and different fabrics/colors as you noted, but otherwise virtually identical.
I don't think one year is any better/worse than another. The more important thing especially with leaks is be how well the maintenance and up-keep has been maintained. Any trailer will develop a leak over time if the seals aren't inspected regularly and recaulked as needed.
2011 Chevy Silverado Crew Cab 4X4
2009 210 WBS