The elephant in the room is health insurance. We have a system where even if you have a fairly good income, buying insurance as an individual (or as a small company that isn't buying in a volume high enough for insurance companies to want to give you a discount) means that you'll in all likelihood be paying a lot more for a lot less coverage. The ACA attempted to solve this by having insurance companies offer plans on "public exchanges" by state and then subsidizing the costs, but because most people making good money get insurance through a job with benefits rather than buying it directly, in practice there aren't really any options on the public exchanges calibrated for people with high incomes. (Plus, if you live in a red state, they've likely refused to take the subsidies, which means either the prices are higher or the plans are even more meager based on what the insurance companies expect people without benefits through employment to be able to afford, or both).