In the event of crash
After I install my pfsense box and all my settings are configured, what would happen in the event it crashes or needs restart. Would the bootup process be automated so If I'm not there it would be back up and running? Id like it to be automated and such.
If it crashes, then generally a crash results in a frozen machine, the only solution to that is a reboot. In that case if you want it automated then I suggest something like this that monitors the router by pinging it, if the ping fails a number of times then it powers off and then back on to reboot the router, you can set up the delays etc so it doesn't jump in too quick.
There are others that monitor the internet connection, these I don't recommend as the internet could go down for reasons that are nothing to do with the firewall.
There is a also a script I've attached that can be run, it's called by a cron event every five or ten minutes and monitors the WAN connection, this time by pinging a WAN address, if that fails after a number of attempts then firstly it will just set the WAN interface down and back up, if that doesn't restore things then it will reboot pfSense.
How would I install or copy over a .sh file?
WINSCP is the easiest method.