It’s a pretty standard bandwidth/latency tradeoff in my view: email is high bandwidth (it’s in writing, you can re-read, etc.), whereas phone is low latency (several back-and-forth explanations can happen in seconds). Each has its place.
If social anxiety is a factor, that’s a perfectly valid, but separate, issue.
I think a lot of companies view their free plan as recruiting/advertising — if you use TailScale personally and have a great experience then you’ll bring in business by advocating for it at work.
Of course it could go either way, and I don’t rely on TailScale (it’s my “backup” VPN to my home network)… we’ll see, I guess.