@jefftv,
I do something similar with the free version of
http://www.firedaemon.com/product/firedaemon-pro.
I have a headless Windows Server with all my files on that I access from various devices through out our home.
Obviously I do not want this system to have auto-login on startup or leave a user logged-in all the time.
It actually works really well and rather than leave this system on 24-7 I use another program
https://www.green-it-software.com/ to control sleeping and waking the server when I need it.
The main downside I have come across is the fact it is regarded as an unsupported way of running MC.
Additionally program upgrades have to be run as an application rather than a service, as does any program housekeeping too.
So in these situations I have to login to the server, kill the service, run the application to do what I need then restart the service and logout again.
It would be fantastic if MC could be split into two, a server that runs as a service and a client that runs as an app.