He said he has two Steam accounts so it should be easy (LOL).
- Set up a VM.
- One Steam account to your metal Windows install and one to the VM.
- Do the family share thing.
- Set your dedicated server to PVP mode.
- Have the VM based character mule things to the metal account’s approximate base location and place the items in boxes.
- Log off the VM account.
- Log on to the metal account and loot the boxes.
How server transfers work on the dedicated server, I have no idea.
If you however want the characters to be in the same clan you will either need a 3rd person or a second CE license. A second CE license will additionally allow the VM and Metal characters to be on the map at the same time.
All that said though, why not just use the Admin Panel on the Metal account in the first place? Then you can just spawn in the wanted items.