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1. Never once seen an issue with USB-C to HDMI or VGA connections. It doesn't even make any sense since MacBook Pro users with external, third party monitors are an extremely common combination.Last year I had a lot of problems with this. It was pretty common[1] that USB-C to HDMI cables would work at first and then stop working in a particular port. Sometimes rebooting helped. Sometimes swapping the cable for another in the same port helped. Sometimes using another port immediately helped. There was never a good explanation for why this was happening; most resources blamed the cables. After some software update last year, suddenly all these bad cables are fine in any port.
As of this summer, there's a shiny new issue where connecting to GMail (at least) from System Preferences doesn't work, which I discovered through changing my password recently. SysPref claims it needs to open a Google login in Safari (even though that isn't my system browser!), but when Safari opens, it's to a blank page. Again, searching makes this seem like a pretty well-known problem, but no one has a solution, and Apple seems silent on it, and enough people do not have the problem that a common response is that those of us experiencing the issue must be doing or have done something wrong. And maybe we are(!), but I'd sure like to know what.
> 3. If you have a tech support issue go into the Apple Store and work with them 1-1.
Well, that literally hadn't occurred to me (for problem 2, above); I would have assumed store employees don't know anything one couldn't google immediately?
[1] I was quite annoyed that this went on long enough for me to have an opinion like "pretty common" for these connections not to work sometimes, over more than half a dozen such cables.