Autostart VMs - Make sure PfSense is running before launching anything else, then launch Plex and others if need be. Put files - C:\Windows\System32\GroupPolicy\Machine\Scripts\Startup and C:\Windows\System32\GroupPolicy\Machine\Scripts\Shutdown (replace start with stop or suspend)

vm_start.bat

@setlocal enableextensions enabledelayedexpansion
@echo off
set vmware_path="C:\Program Files (x86)\VMware\VMware Workstation"
set vms_path=C:\Users\MY_USERNAME_HERE\Documents\Virtual Machines
set ip_of_pfsense="PFSENSE_IP_HERE"

echo Starting VMS
echo ============

echo - PFSense
<nul set /p = "- Waiting to boot "
%vmware_path%\vmrun start "%vms_path%\pfsense\PfSense.vmx" nogui

:loop
set state=down

ping -n 1 %ip_of_pfsense% | find "TTL" > nul

if not errorlevel 1 set state=up

if %state%==down (
    timeout 1 /nobreak > nul
    <nul set /p =.
    goto :loop
)

echo ... Booted

echo - Plex
%vmware_path%\vmrun start "%vms_path%\plex\Plex.vmx" nogui

endlocal