Yeah it should be rare now for a payout to miss being in the next block due to me being asleep

I've written some (reasonably simple) scripts to queue the payout to be sent just after the network block appears when it's matured.
It's still a manual step to 'queue' that command, but I can do it any time in advance after I've processed the payout.

Processing the payouts is where I spend a lot of time checking everything is all OK, but the transaction itself is just there ready to be sent once it's been processed.

I was actually testing this over the past week and the first night I ran it, the PC with all the bitcoin and monitoring software on it failed due to both raid1 disks, that contain (only) the internet accessible bitcoind (no wallet), failing during the night
Fortunately it seems it was a controller+linux glitch, and upgrading linux and moving a SATA cable brought the 2 disks back to life

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