Hard to say, upgrade means going to a junior base which are almost universally high COL areas and you'd need to either move there or rent a crash pad for several months to several years until you can go back.
In my case, I'm lucky enough to have 0 ex-wives and no kids to put through college so I'm in a comfortable position money wise. It would take a pretty big chunk of money for me to take the hastle to upgrade until I could hold my base.
Working in that industry, in a jet with seats for 8 non-crew passengers (in ~50% more space than a Lear 45) most flights have 2-4 passengers, 1 is common, 7-8 hardly ever. Also you need the 172 if you want trained pilots in your 787.