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.
As a pilot the problem with upgrading early is seniority dictates QOL. A junior captain needs to work a junior base, fly a junior plane, and get whatever crappy trips are left in the schedule. That means that a senior First Officer would have to move or commute to a new city until they build enough seniority to go back to where they want to live all while working the worst schedule, or even worse sitting on reserve. Absolutely not worth the pay bump when you can wait a little longer and not have to deal with all that.
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.