80/20 Rule
The 80/20 rule is simply this: Invest in a plane that best serves 80% of your flying missions.
This may mean that you need to think outside the box for the other 20%. For example, if 80% of your missions are weekly day trips within a 300-mile radius and include you and one other company executive, an agile single engine like a Cirrus SR22 could fit the bill, even if 20% of your trips are coast to coast. Commercial or charter jet travel may make the most sense for the 20% of your flights that span from one coast to the other.
On the other hand, if you regularly load up an entire team to travel from New York to Miami for multi-day sessions, a cabin-class Piper Mirage could best serve your mission, even if the other 20% of your trips are hops from New York to DC. Small charter or aircraft leasing could fill your short leg needs very well.