I started this thread with a blow-by-blow so why stop now
Can't find any place locally that has everything in stock - bearings, oil seal, races, etc. So, it looks like I need to order it online. That means I've been asked "by the powers that be" to move the trailer out of the garage. I slapped the hub and bearings back together with the old ones without any grease. I figured all I need to do is roll it out of the garage and across the street - and I can do that without grease and a oil seal.
When the bearing kit comes in, I'll be pulling the races as well and then putting it all back together. For the other side - I'll have a look at how it is as well and may or may not replace the bearings on that side. I'm guessing the only issue on the other side is that it's got some really old grease in there from when the trailer was first put into service.
Side note - I found a faint "made in china" on the bearings that I pulled out so I assume it will be an upgrade to timken from the current bearings.
Once again - thanks to everyone for their help in this project and I'll follow up once the new parts are in.