I don't think Gary was ever afraid of tapping into the non traditional markets.
The mission presented to him when he was brought on board was to get a legitimate national TV deal in the US. In order for that to happen, he needed to get more teams particularly in the south, which is exactly what he did.
The southern movement started almost immediately under his watch with moving teams to Texas, Arizona, and north Carolina and then expanding to Tennessee, and Georgia.
Infact, the nhl had already started the process of expanding their southern exposure prior to bettman with new teams in Florida, and California.
Most of these franchises appear relatively healthy and are still standing, so I don't think there would have been much apprehension by the time they got to 2017 and Vegas came in.