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There's a great method to allowing one to access a machine behind a firewall by creating an outgoing listening connection: Remote into Linux workstation behind a firewall

My question is, what's the best way to make sure this connection is always up in a safe manner when I'm not at the desk? cron? (Reboots, power outage, etc)

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up vote 0 down vote accepted

I assume you are talking about the SSH method from the accepted answer? The OpenVPN answer would be far more stable, since it is designed to function as a VPN, packaged versions of OpenVPN include startup scripts, and the OpenVPN daemon is very good about resuming a connection after a restart.

Anyway, assuming the SSH solution, you should really be taking a strong look at the autossh program. It is specifically design for the purpose of bringing up SSH port forwards automatically and reliably.

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