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.
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.
I wanted to host a Minecraft server for some friends, so I got cobbled together a PC out of some spare parts and put Ubuntu server on it. Over time I added an emby server and tools to get media for the emby server and that was good for a few years. Then I moved and had some more space and fell way down the rabbit hole of used enterprise gear.