I haven't seen this behaviour and it may have some relation to the lack of actual state reporting devices - as you suggest. I assume the xAP hub is left running 24/7 on the Cortex machine and xAPFlash is not being restarted.
Is it the xAPFlash button that doesn't control the device or is it the Cortex device that doesn't show it's status in xAPFlash when Cortex starts - the latter could be due to Cortex's 'info' reporting ?
xAPFlash typically sends 'toggle' commands to a device if you are just using the basic mode of operation and so until Cortex knows a state it won't be able to change it. What device in Cortex do you have that you are controlling ? Does it report a xAP state when you start Cortex up ?
Re two line labels . you could instead use a text field instead of a label which can display any number of lines....
K