A merge to a new branch based on the head of trunk should be no different than a merge to trunk itself. The secondary merge of the newly merged branch to trunk will be trivial. I still often do exactly what you propose so that I can test and debug the merged code before committing it to trunk.
So the real question is, merge from trunk to branch first or just merge from branch to trunk and be done with it? I usually decide based on two things. Is the branch obsolete after this operation? If so, I merge from branch to trunk. If not, I ask myself which changes am I more familiar with and I merge FROM there. For some reason I find this easier. If the merge is painful due to conflicts, I sometimes do the merge one changeset at a time. Have you figured out whether or not the conflicts are due to white space issues such as new lines/carriage returns, tabs/spaces or other reformatting issues? jlm