Wow, I was really surprised to find out rf2 only has a windows dedicated server :S I didn't even consider that possibility before renting a VPS with the thoughts of hosting a server.
Anyway, I just read through the thread, will look in to setting up wine etc, never done so without a GUI, although now that I think about it, didn't use the GUI when I did anyway, should be good learning regardless

Thanks for the thought of that!
When/if I get it running I'll post a guide to getting it running for others hopefully.
Well I got it running, but then the VPS host shut that down just about immediately

No Wine allowed they say, pretty sad, was working quite nicely, only real snag for which the information wasn't readily out there for was that you must be running steam with an account that owns rF2 for the Steam version, everything else had already been covered in other threads.
This was the process on Debian Jessie, everything should be able to be google'd for more specific directions:
Install LXDE and tightVNCserver to get a desktop you can remotely connect to
Install Wine
Install Steam via VNC through Wine
Download rF2 through Steam (actually did this natively through steamcmd then later moved it over to the Wine steam install dir, steamcmd is quite a bit faster in my experience)
I had to make the vmod locally and uploaded through ftp (so Install vsftpd)
Also, an issue, because Wine couldn't run rFactor2.exe to install the workshop items, I had to download the cars/tracks manually and install them through modmgr.exe (also moved modmgr to the rFactor 2 root directory because I couldn't get to the steam install path through the directory browser, can probably unhide /.wine somehow but this was a quicker fix.)
Then that was pretty much it, pretty straight forward.
I'll be trying a VM next, see if the VPS host shuts that down, if so I'll give up and wait for a Linux server (this VPS is way too cheap for me to discard)
Just as a side note: I couldn't help but notice
https://steamdb.info/app/400300/subs/ which I couldn't subscribe to, could this have a Linux version maybe? Or just a version that doesn't require a purchase? Either would be good, but the former is the dream
