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Myself right now I'd probably take it with me - in fact that's that I'm planning to do in a couple of months - but it sounds like my needs are a bit less than yours, and i can do some stuff just over LAN and on the 'server' (which is also a laptop) itself.
For more, I think I'd also ask a friend like you're thinking.
I did that before with a relative - just had to ask them to restart the server every now and again!
About trusted encryption keys, I did it with a simple password for boot encryption, that my relative knew, so in the event of theft it'd still be hard for thieves to get anything; but after boot I'd ssh in and unlock the second disk with my own password, then start up the services.