I would compare Wheels Up to a condo timeshare, kind of.
You would have to do a fair amount of research to decide if Wheels Up is worth your while.
The Good
- smaller planes means cheaper flights
- two pilots
- the social features allow interesting things like common destinations and airport transportation, which would be great for sports fans, etc.
The Bad
- it appears Wheels Up is trying to package seats with multiple clients on the same flight (not so private)
- most of the planes aren't owned/leased by Wheels Up
- NetJets has a working business model, most smaller services don't
- $15,000 first year (plus time), $8,500 second year (plus time)
Source: commercial pilot who follows the trade press.