Okay, did the updates and had no issues. Step by step this is what I did:
1) Download the Dealer update to PC (Harley_POI_Maps.zip). Open ZIP folder, highlight and copy both items listed: nng (File Folder) and swdl.iso (Disc Image File).
2) Open USB thumb drive #1 with NOTHING on it, and paste the files.
3) Download the Boom update to PC (swdl_boombox_6.5GT_CVO.1.21.2.1). Open ZIP folder, highlight and copy both items listed: swdl_boombox_6.5GT_CVO.iso (disc Image File) and swdl_premium.iso.md5 (MD5 File).
4) Open USB thumb drive #2 with NOTHING on it, and paste the files.
You can use one USB thumb drive, but be sure to erase first files before pasting in second files. I had two thumb drives, so I did them separate and saved myself a trip back and forth to the garage.
Next:
1) Turn on bike in Accessory mode
2) Turn on InfoPainMent system and wait for initial boot-up
3) Press Navigation button and WAIT until it says Navigation is ready
4) Insert dealer Update thumb drive and wait as it authenticates (15-20 seconds total)
5) Display says "make sure in accessory mode", hit yes, then start update.
6) Watch Package progress 1 of 1 and Overall update for Dealer update (took mine less than a minute).
7) Display says "update complete, remove USB drive". Remove drive, system reboots.
Next: Repeat the same process for the Boom update using the USB with the Boom files on it. This one takes a bit longer because there are 10 packages to update. Mine completed in something like 5-7 minutes (wasn't really paying attention).
1) Turn on bike in Accessory mode
2) Turn on InfoPainMent system and wait for initial boot-up
3) Press Navigation button and WAIT until it says Navigation is ready
4) Insert BoomBox Update thumb drive
5) Display says "make sure in accessory mode", hit yes, then start update.
6) Watch Package progress 1 of 10 and Overall update for BoomBox update (took 5-7 minutes).
7) Display says "update complete, remove USB drive". Remove drive, system reboots.
I then went into system and checked software versions and everything took.
Good luck guys!