You might consider using openvpn so that any tunnels are TCP over UDP
rather than TCP over TCP as when using SSH.

Also, you could use the gmail/gdrive over fuse (with encryption as you
see fit) for file sharing.
One option I've thought about trying someday would be to use md raid1
with a dbd and the --write-mostly flag where dbd is on top of say a
gmail fuse device--thus work gets synced remotely but you get
near-local file access speed.

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