Hey @WeeboDev, Welcome to the Local Community Forums!
It’s hard to say why there’s an issue without seeing the actual Local Log. Local does a pretty good job of redacting sensitive things, but if you don’t want to share that log with the forums, I’d recommend taking a look at the Local Log to see what sorts of errors are being reported in it. Here’s a topic in the Forums that outlines how to get that log for you to review:
One thing I’m curious about – are all of these sites running at the same time? Once the computer is restarted, are you still able to start each site, or do you have to re-create the sites again after restarting?