I'm still not seeing how there can be ANY commercial pressure.
Oh boy......welcome to the world of carrying non-aviation people around (schedule or charter).
Imagine you arrange a share sight seeing flight that just so happens to go from A to B. Despite your warnings about the possibility of the flight not going Lady or Gent you arrange to share the flight with then goes off and arranges a meeting/family reunion at B based on the expected flight.
He/she turns up at the airport A on the day and finds you saying "in my opinion it's too windy/cloud base to low/forecast poor at destination".... or worse still you are in flight, wx turns to pants, you tell him/her you are turning back...........
In the commercial world regardless of the warnings on airline tickets/websites there are commercial pax who book flights that they regard as simply
having to operate, and operate exactly on time, in order for them to get to meeting/wedding/make a connection on time, and believe me they will apply pressure/make noise if there is a hiccup, even it is just a few minutes late due a slot delay........and many are not interested in any airmanship reasons you can offer as to why you are not operating as planned - they had arrangement, they want to travel..now.
I think you are being naive if you think that because you use wingly and pre-warn fellow travellers you are going to be exempt from "commercial" pressure.
I can only repeat my previous opinion I see wingly being fine for local area flights - I think it's a completely different and "iffy" game using it to offer to take non-aviators flights from A to B.