Hey @CharlieC! Welcome to Local.
It does sound like there might be something going on in Local when you are trying to shut down the individual sites and it doesn’t complete the process without quitting Local to force it.
Can you please provide your local-by-flywheel.log file? See this Community Forum post for instructions on how to do so:
As for completely removing a site, Local does make adjustments to your hosts file for the sake of creating the routing necessary to connect a browser to the Local site. This might be the case but the log file should give us some more insight into that error as well.
For the site that gives you a 404 response, does it have any banners in Local suggesting there might be something to fix, such as this
