While no one is “condemning those who play by the rules” or “demonizing the 1-percenters”, and one is “careful not to over-moralize about the choices other people are almost forced to make”…
some may say that a planned early retirement with the specific intent to game the system for need-based financial aid for college costs may be unethical, and an example of what some people may resent about a system which seems to help the wealthy and affluent become more so, while syphoning dollars out of the system which were originally intended to help those with "need", not those with "game".
IMO, the insanely high costs of our tertiary education system are immoral. We tell kids that they MUST go to college. Then the colleges and the banks soak them and/or their parents and yoke most of them to debt that can't even be discharged upon death.
As far as I'm concerned, finding a way to beat being fleeced isn't immoral, and claiming that people who find a way to do so is the wrong way to look at the problem. People who beat an immoral system aren't the problem.
The system is the problem. The solution is to change the system. In this country, that would mean going back to heavily subsidized public universities, as we used to have in California and in other states.
("Heavily subsidized" means "affordable without loans.")
