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Both questions actually could be related to an antivirus or software firewall on your desktop. I would go into your WorkSpaces console to see if the instance is showing Unhealthy (this would be a result of the Skylight service not being online).
Concerning your first question, this sounds like it is an issue with the client side firewall settings. Authentication goes over 443 (TCP), but the actual streaming of the Workspace is typically port 4195 (TCP & UDP) for web access. I would take a look at the port requirements for your WorkSpaces to confirm they are correct (again this points to possibly antivirus software/firewall enabled):
https://docs.aws.amazon.com/workspaces/latest/adminguide/workspaces-port-requirements.html
The second part to your question concerning Skylight would be that there is an issue with the Skylight service starting. Here is a previous post on troubleshooting the service:
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