I’m trying to figure out how to resolve conflicts that arose when I updated my local workspace with changes on the server side, and I’m pretty confused as to what’s going on.
First, with one conflict, it was all exactly as I would have expected:

Automerge failed due to conflicts, but the options I expect are presented: manual merge, take local, or take remote.
However, in the very same changeset but with a different path, I don’t get an option to merge.

Why not? And how am I supposed to ever fix this conflict without being able to merge at some point along the way? Is this due this being an add conflict rather than a content conflict? If so, is there a way to force a manual merge so I don’t have to write my changes again?
This is because in example #1 there are 2 edits to the same file. You can resolve the conflict’s by picking which bits, or which version, of the two edits to the file you want to keep.
In example #2, there are 2 additions of the same file. TFS 2010 cannot handle this, so gives you the choice of which file version do you want to keep, the one you added or the one added on the server. I don’t think it expects two people to add two versions of the same file, and that someone would want to merge the two versions together.
Conflict resolution has been improved massively in TFS 11, but I don’t know if it will cover this case.