Welcome to the Humminbird Side Imaging Forums Tyler.
I hate that you are trying to take this on days before a week-long trip but we can hopefully provide some answers for you.
Software updates: What software version is each unit running now?
Unless you just need to, I would not update your units or the i-Pilot Link just days before going on a trip. If something goes wrong you may not be able to use that piece of equipment for your trip. If it all works okay now I would leave it until you return. The 7.020 software update added support for the AutoChart maps, Ethernet sonar sharing (which you should already have been able to do with the 899/999 units), and some fixes for the using with the i-Pilot Link system. I would read through these to see if these are any that you need fixing at this time and then decide to update or wait. If you update the units to the 7.020 software, you will also have to update your i-Pilot Link to the 2.020/2.050 version software. Either unit can be used to update the software on the i-Pilot Link Controller and Remote, there are directions on how to do this on the Humminbird web site.
When you update the units I would take all map/memory cards out of them, disconnect the Ethernet cable, reset the units to the factory defaults and make sure that the software update file for that unit is the only one on the memory card I use. I would also rest to the factory defaults afterwards as well.
You will need to use the HumminbirdPC program to upload the *.GPX file of waypoints to an MMC/SD/SDHC memory card before installing it in the unit.
I think that Doug Vahrenberg’s YouTube videos are about the best option for learning to use the i-Pilot Link along with your units though I’ve not watched Dr. Jason Halfen’s vidieos yet.
http://www.jasonhalfenoutdoors.com/LinkIndex.htmlNo apology needed for the length of your post, I just hope that I have not further confused you (especially with the software update part – it’s just confusing right now).