I agree with the comment that it is critical mass.
If you have people in your area who like the same stuff you do, no need to pay to play. But if you don';t, then hiring someone to help you may make sense. But, it can be challenging, as you have noted, to make sure the person you are hiring is going to provide what you want.
We have a good community of ocean paddlers here in NorCal. Definitely have that critical mass. One of the challenges for people not part of the group, though, is to get in with the group of more advanced people so you can paddle with them. Many think it is cliquish. But in reality is is that liability issue. These advanced paddlers understand that not everyone paddles at their level, but they want someone that they know will paddle within their level. Not everyone does.
The way in is often a bit of paying to play - most of these advanced paddlers are the instructors at local shops, and if they see you can control yourself in the class (taking appropriate risks, avoiding extreme risks), they may invite you on other paddles.
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