1) I have successfully loaded the data into a test Feature Layer (hosted) in ArcGIS Online from a shapefile (see below). But shapefiles do not contain attachments - I need to load it with attachments.

2) Kind of a side problem, but I haven't been able to zip up the folder containing my FGDB with attachments in windows explorer. I believe ArcGIS online requires the folder to be zipped. It's not a space issue. I have 200 GBs of free space. The FGDB with attachments is under 5GB.
I have tried to append a FGDB of the original data (containing attachments) that was already zipped up in windows. It errors out;


Any advice would be much appreciated. I attended to a conference recently and I believe I heard some advice to move away from hosted feature layers, but at this point, I am just trying to maintain and improve what we currently have before I move forward.