I did reply to your PM, so we don't go too far off topic.
As for signing;
MacOS: I have got this kinda under control now, even though it's not always "easy".
I tried using sandboxing, but I keep running into issues, so I sign my applications without sandboxing (for now anyway - since the sandboxing idea may not be all that bad after-all).
These days, as a developer that is not using the Apple App Store, you can get a cert for free. You have to register as a developer though, but as I understand you do not need to pay (my payed one just expired and I'm not renewing this until I put something in the app store).
So I sign to have the users not see the message about unsigned applications, and have firewalls like Little Snitch not block network traffic because of that.
I'll PM you with the details on how I sign my apps.
Windows: I'm not signing anything here yet - getting a cert is just too expensive. But ... since Microsoft mimics Apple ideas, this will be unavoidable in the future.