Oh, we've got lots to talk about! I'm in the same situation, my TM only fits in my garage by removing the awning (it goes back on just fine) as well as swapping the side courtesy lights (2 on the curbside and 1 on the street side) with lower profile LED fixtures. Removing the awning alone gave me around 2 inches, because the lights also stick out. Each fixture replacement was another inch per side. So now, the corner clasps are the widest point, and I leave those open whilst bringing the TM in and out.
I have posted a picture on another thread of the awning modification. There are 8 screws that hold it onto the side of the TM. That and a lot of caulk. So, unwind the awning, unscrew the screws, have a helper lift and peel away the caulk. Once the awning is off, you'll see the weight rests on metal brackets, and the screws were just to prevent it from pulling away or flipping off the top. So, two little slide bolts later (seen in the photo) and the awning is as stable as stock. Removal is a simple flick of the two bolts, and then I flip it onto the roof. Reinstallation is a simple reversal, and I can make the manipulation by myself. It can most certainly be done for a trip-by-trip on/off, since that's exactly what I do
I don't think there's any real need to caulk those holes; they open into the same space that the weepholes do, so they're really just like more weepholes...
Search on my name for the photo, else I'll find it for you. As spring more fully arrives and I pull the TM out for work, I'll take more pics to show you more of what we did, and how it just fits in it's space.
Ah, here's the post with the photos.
http://www.trailmanorowners.com/foru...9&postcount=71