There is, in general, a very big gap between private and cost-doesn't-matter commercial. And, no, I can't speak to what flying private is like.

Flying can still be a hassle flying business/first mostly because of cancellations/schedule changes--which can still happen otherwise because of weather, air traffic, etc.--but is less frequent I assume. A lot of the hassles of commercial flight (security lines, lack of overhead space, airport crowds in the waiting area, cramped seating, etc.) can be mitigated to a significant degree however.