early_riser

Since you’re just sharing things within a small group, I think it’s safe to give out your IP or a domain pointing to it. However, you need to put your services behind a DMZ. Make a separate VLAN on your network and put the Pis behind it. Make sure traffic from your private LAN can enter the DMZ but nothing from the DMZ can go to your LAN unless it’s return traffic for a session started in your LAN. If a machine in your DMZ is compromised, it shouldn’t affect your LAN.

Private email. Very nice 👍

Are you hosting on win server? I’m genuinely curious, not trying to shill Linux though I prefer it on the server side, believe me I’ve been on the receiving end of that. How do you manage it? Do you have your home LAN set up as an active directory domain? Do you use mostly Powershell or the GUI? What do you have running on it? It just seems like everything on the server side assumes you’re using Linux and the only stuff that runs on Win server is stuff made by Microsoft like MS SQL server or IIS.

I also like LocalSend. Not quite as automagical as airdrop but it’s cross platform