Join Date: Apr 2005
Location: SW Washington, USA
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#1: Not a problem. If you search around for pics of loaded bikes (e.g., crazyguyonabike.com) you'll see this is pretty much normal.
#2: I don't know why this usually happens, but on most bikes I've seen, racks and eyelets aren't flush in the same plane. When finally mounted, they should be. Either bend the rack's mounting plate slightly, or use a standoff (a small metal cylinder, like a very thick washer) -- filed down to the appropriate angle, if necessary -- so that there is a solid connection. There should be no threads visible on the mounting bolt between the plate and the eyelet. If there are (or if the rack contacts the fork and takes strain off the mounting bolt), you have a weak link. This would allow the bolt to flex slightly, and eventually break.
It's tough to describe this, and maybe I misunderstand your point #2. But the mounting point (rack-bolt-fork) should be solidly mated, with no wiggle room.
#3: Not clear to me..... But on my bike, even though the fork has two eyelets at the dropout, I can only use one to mount the fenders AND rack. Not ideal, but the geometry just doesn't allow putting a fender strut or the rack on the other eyelet. This puts more stress on the mounting bolt, but so far so good. If this is what you have to do, keep an eye on it.
Of course, different racks have different angles and mountings. I have a Blackburn front rack (and a different bike) -- YMMV.