I installed my SE air cleaner along with a black horn cover and black air cleaner cover. I have to install my VH fuel pak and black 2 into 1 Thunderheader. I have been putting this off for a week now because during the exhaust install I need to remove the clutch release cover, and the 4 bolts behind the cover to install the exhaust bracket. How much (if any) oil will dump out when I remover this cover? I already bought a new gasket for the cover. Also, by removing the 4 bolts behind this cover, will I have a chance of starting a oil leak in this area? I am installing this on my 07 street bob.
Almost forgot, I also bought the heat shields for the header, should I install the heat shields before or after I install the header, I want to minamize my chance of scratching either the header or the shields. It says nothing about the shields in the instructions.

 

Much of the oil will dump out. Do the job right... drain the transmission, then remove the clutch release cover. The trans only holds 28 ounces, so it's not a big deal to buy a quart. If you remove the cover, clean everything up, then install the new gasket correctly and you will not introduce a leak. I've done this procedure many times with no leaks. Follow the instructions in the manual very carefully for bolt torque sequence and torque value.

Always install the heat shields last. Many shields, if already installed, will not let you get a socket on the exhaust stud nut. Again, torque the exhaust nuts by the book and use new exhaust gaskets.