This sounds like libinput or touchpad-synaptics issue. Can you please check which you have installed? xserver-xorg-input-libinput xserver-xorg-input-synaptics
Your input fixed the touchscreen / trackpad issue at boot and when in use, but realized that if I disconnect the screen from the track pad and keyboard (Surface style) the trackpad does not come back until I reboot.
Sounds like just disconnecting without termination of the process crashes it. It cannot restart unless told to or re-initialized (Which rebooting re-initializes.)