I just installed the sissy bar extension and luggage rack last weekend. It was definitely a bear to get those four replacement bolts in. I was cussing that little POS allen wrench and wishing for a couple of nice hex-hed bolts, especially for the two on the bottom. I did finally get them screwed all the way in without stripping them, but it was a real bitch. If you are going to have to remove them again to install the extended sissy bar I would suggest replacing them instead of reusing them.
I have a small tail bag on the way from Newenough, just big enough for my rain gear and a few more things. I also ordered a little tank bag just big enough for wallet, keys, shades & cell phone. I have a fork bag for my tool kit, sidestand plate, maps and some duct tape (the essential repair tool!). I don't use the tool box. The lock was gone when I got the bike. It has duct tape on the hinge and it is closed with a zip-tie.
"Shutting up rarely leads to anything bad"
VROC # 28175
-2004 Vulcan 1500 Classic 22000 miles
-1995 VN750 (Back home again!) 25000 miles
-1995 Suzuki DR350 Dualsport 1720 miles