Ha ha, I tried something similar when I had to go to Thailand for my wife's treatment. And failed spectacularly. Fortunately, my laptop had all the files. I didn't have Tailscale at that time.
My Desktop, WoL on, tested to be working Android Phone, always on
All have SyncThing installed. Mobile had Tasker installed.
So, the idea was to have Tasker monitor a folder inside SyncThing, When I need my computer, I put a file inside that folder, when Tasker finds that folder, it sends WoL to my desktop, and deletes the file, Computer wakes up. When I see the file deleted I know, the beast is now awakens ....
When I actually did try that from Thailand, the file did not got deleted, nor the beast woke up.
What happened? Turns out, my mobile restarts automatically after some time of inactivity. Which, locks Tasker out, and the whole process fails.
So, operation wake the beast was busted.
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