Serious expert help needed!

I have been pulling my hairs out over the last few weeks troubleshooting network connectivity in hassio (outbound calls failing regularly, but only some of the times). I have described my environment and relevant logs in this document.

I hope someone can help me get this sorted! Never had this kind of issues before. I think I have it isolated to hassio (host VM has no issues).

T H A N K __ Y O U !!