How do I determine the order to apply change sets from multiple work items?

Thanks very much for this. Does this mean that in general accepting change sets from work items is not a good approach and a workspace-driven approach is recommended?

I would rephrase somewhat ... if you are accepting overlapping change sets from multiple work items, then the Pending Changes driven approach is recommended ... but if the change sets are not overlapping, or you are only interested in a single work item, then accepting change sets from a work item is fine.

ok but how can you tell if the change sets are not overlapping?

Try to accept change sets from just one work item, and see if you get a gap conflict.  If you don't, you can just accept.   If you do, you should switch to the workspace approach.

ok so if I understand correctly, a gap conflict does not actually mean that the change sets for the work items I am interested in are overlapping just that I am skipping accepting an earlier change set and I cannot easily tell if the change set causing the gap conflict is the earliest change set in the group of work items I want (and therefore would be ok to accept) or a later out-of-order one?