One problem is that it does not support DNS tunneling if FreeBSD is your client.[1]
Item: we (rsync.net) would be willing to pay for development that gets sshuttle to work properly and bulletproof on FreeBSD. In fact, we would be willing to pay for sshuttle development in general. Email us.[2]
Also, what is up with this new fork ... which speaks from the original authors point of view and, in fact, has his own personal notes cut and pasted into the README. In fact, the contact information is the original author - Avery Pennarun apenwarr@gmail.com - what's going on here ?
[1] No, the note about IPFIREWALL_FORWARD does not fix this problem.
[2] info@rsync.net
I ended up creating a proper VPN via a microtik router and have enjoyed the superior performance compared to sshuttle, though it was several orders of magnitude more effort to get going! sshuttle was almost too easy to get up and running :)
If you need something more resistant to DPI, check out stunnel or obfsproxy as carriers for OpenVPN. Switch ports regularly as well. You needn't change server config to do this: just use iptables to forward stuff so your server's stunnel daemon is listening on hundreds of ports.
I've used it extensively on Yosemite.
EDIT: Appears this fork does support Yosemite, it's even installable via Homebrew.
An OpenVPN server can go from zero to done in under 5 minutes (for HN readers, less) with a Docker container: https://github.com/kylemanna/github
... Only recently had issues during the parade using with the Linode IP range. DigitalOcean no problems.