Welcome to the list!
From cut-away views I have seen of that seam (both demo piece of roof and pictures), it seems to me that water is extremely unlikely to be able to get inside the coach from there. The roof fiberglass sheet goes down into the "J-channel" behind the drip rail, and the caulk helps to keep it in place there. There are drains in the bottom of the channel. If water were to get inside the coach roof it would have to go around the bottom edge of the roof fiberglass sheet and then wick upwards ...as I say, it doesn't seem at all likely to me that would happen. The primary concern I am aware of with that seam being checked/recaulked at least once a year (to maintain the Winnebago 15 yr warranty on the roof) is that if the caulking is neglected for a long period and deteriorates enough, the roof sheet can be pulled out of the seam by high winds (either a storm or while driving). The result for some owners has been losing chunks of the roof, or most/all of the roof being peeled back like a sardine can. I'll see if I can insert an illustration of the roof side cross section below.
On an '08 model coach, I wouldn't worry about it. I have my side seams checked at least once a year. Sometimes they need minor repairs, and sometimes most/or all of the caulk needs to be replaced.
BTW ...there is lots of info available for "previous year" models on Winnebago's website. You can download a 2008 Sightseer brochure at
http://www.winnebagoind.com/products/previous-models/2008/pdfs/winnebago/08-Sightseer-Brochure.pdf. They also have wiring & plumbing diagrams, which can come in real handy for trouble-shooting problems later.