Hello terrible_towel
Firstly, sorry to hear you had a seemingly negative support experience - if you could please PM me the SR number I would like to have a look from our side and loop in my management with regard to this case.
As a daily practitioner of worst-possible-scenarios (mostly user/admin/architect-caused) I do understand your concern over clicking the button that is in reality going to do a lot of things and potentially reacting unwanted states.
From my own research and testing of upgrading vDS from 6.0 to 6.6 (on HOL, nested-homelab and physical) I have never encountered an issue that caused vSAN cluster to become partitioned (as opposed to migration testing ripping out a used uplink and migrating to a vDS which recovers in ~30 seconds on a HOL cluster).
That is not to say there is no possibility of a negative impact, there are known issues (and apologies but I am going to have to get this kb remediated as it makes it sound like it is NSX-specific when it does not appear to be so):
https://kb.vmware.com/s/article/52621
As our documentation advises, please take a backup of the vDS configuration before upgrading:
Upgrade a vSphere Distributed Switch to a Later Version
When it comes to networking change guidance I am generally overly-cautious, but this is borne of seeing how bad it can go when someone doesn't understand and/or know their network layout and/or the potential impact of the changes they are making (and wants to make them on the fly just because it is possible), thus I generally advise *if possible* that planned downtime or changing this during non-production hours is the best course of action. That being said, upgrading vDS is relatively low on the scale of things that you can change that have the potential to really break things (e.g. MTU/VLAN/physical changes).
Bob