Life wasn't always this complicated for pilots. For decades the move to the next category of airplane was clear. You started in a fixed-gear single, moved to a retractable single, and as the budget allowed, into a piston twin, pressurized twin and then on to a twin turboprop and maybe, for a few, to a jet. Sure, there were choices to be made, such as to move into a Bonanza or Cessna 210, but the steps from one category to another were obvious. And for those of you who study the AIM far too much, by using the word category I don't imply the FAA definition which is far too broad to be useful.