This thread is getting boring. Let me ask a question for anyone who might still actually be paying attention.
Would you, as a pilot, actually offer seats on your flights? Insurance, regulations, etc. aside, would it be worth the time, effort, and payload hit? It seems that logistical issues for small planes would invitably sink the business model.
In my experience, for anything more than a burger flight, my plane (a 182!) seems to fill up. Bags, stuff, people. When it was the two of us and a dog, we seemed to cube out with stuff. Now that we have a 7 month old, forget about it. I'm sure others travel lighter, but one of the nice things about having your own plane is taking whatever you'd like.
Also, logistics. You can all plan to meet at 9am, but what if the weather that morning suggests you need to leave at 7am. Do you ditch your paying passengers?
What if the flight is delayed, costs more because of headwinds, etc. What if it's less?
How do you handle a diversion, where you land half-way and drive or book a last minute airline ticket to the destination?
I'm not adverse to the sharing economy. I did a stint on Relay ride renting out an extra car that I had. I found the renters to be often flaky. It got a little better when I listed it to pilots only (I eventually moved it to an airport with no courtesy cars) but even that became logistically problematic on occasion. The big issue I had was people acted like they were dealing with a business, rather than just a dude with a car. Thankfully I never had issues with breakdowns, crashes, etc. It did get vandalized by an airport employee, but that wasn't the fault of relay rides.
I've also considered making my base suite available on AirBnB. I guess the reality is I'm not all that interested in having strangers around for long periods of time. Maybe extreme extroverts love this stuff.
To me, the reason Uber X works is because it's immediate, it's for a short period of time, and people can look inside a car quickly and determine if they'd like to take on the risk. If the driver is dangerous, they can ask the driver to pull over and get out. Can't really do that in a plane, assuming you knew that the pilot was doing something dangerous.
Now if Flytenow and similar operations were limited only to offering othering pilots rides, or sharing flight time, then my thoughts on it would probably be different.