I just did this on a transportation bicycle I'm putting back together for when my daughter visits. I hadn't thought of doing it this way before. My brain was just programmed to screw in the bolt from the outside. I did exactly as Eric said, I screwed the bolt in the dropout with the head on the inside. After I put the rack on, I tightened it up with a nut, then washers on both sides of the fender struts and finally a nylon insert lock nut on the outside. An added bonus was that it was easier to assemble the various units with the head on the inside. I could put the struts on the end of the bolts already sticking out instead of putting the bolt through the struts 1st and then trying to locate the threaded hole with the interference of the weight of the accessories. I am sure it is much less likely to come loose doing it this way.

This transportation frame has had an interesting history. I made it as an example of the kind of frame we wanted the XB3 bicycle company in Kharkov, Ukraine (near the Russian border) to make for our charity bicycle project. They used to make the majority of bicycles for the former USSR. It then spent time in the city of Cherkassy, Ukraine at the home of one of the owners of the laser cutting company that makes our main triangle fixtures. Eventually I brought it back to the States with me where it was stolen one rainy night when I hadn't brought it back inside. One of my framebuilding class students spotted riding by while he was waiting at a red light. Eventually the guy was arrested and I got it back. I repaired the repainted the damaged paint and now I am putting it back together again with the bolts in the dropout eyelets pointing out instead of in.