Inside of polyboost (graphite tools in 3dsmax 2010) there is a Swiftloop function lets you place a loop wherever you click. It was inside the polydraw tools in polyboost, not sure where it is now in 2010. If I remember correctly it lets you slide it into place before you release. I haven't used it in a while tho...
Glad you figured it out, but its weird it wouldn't do that on an open edge I'll have to see if I recreate that at some point, I don't think it should do that. =) There are two ways I know of to check the normals. 1) Apply a Edit Normals Modifier to your mesh. It draws lines from each vert showing which way. 2) If you're…