+ AA6YQ comments below
I figured out the LoTW problem. Thanks for your help, Dave!
I went to the Adv button and used the filter duplicate QSO's button. That gave me 170 duplicates, I then went and bulk-deleted them. I hit "Add Requested" and that page once again filled with 170 Q's. Used the "permit uploading" option (which needs to be re-enabled any time you want to use it, I found -- a good thing)
+ that's intentional
ctrl-Upload to LoTW and things look much better.
+ Depressing the CTRL key while clicking the "Upload to LoTW" button has no effect.