If the HOA allows flags, any kind of flag, they will lose.
Even if they do allow flags, they won't necessarily lose. HOAs usually have a lot of discretion to make decisions on a case-by-case basis.
I think a lot of this is pointless. The idea of a principled citizen flying a Confederate flag -- while he voluntarily lives in an HOA with a totalitarian "government" -- is comical.
The Courts have ruled flags as freedom of speech. The HOA will not away with allowing one without allowing this one.
My husband and I are now living in our third condo. There are ***many*** advantages, too numerous to list to list here, of living in a community with an HOA.
The man flying the flag should have carefully read the HOA meeting minutes for the last 5 years and the association rules before buying the property. If he doesn't like the current rules, he should sell.
Our first home was in a neighborhood without an HOA. Soon after moving in, the house next door was sold and turned into Section 8 housing. In one year there were more than 100 police calls to that house for violence, prostitution, and drug dealing. We and the other neighbors were powerless. We even offered, as a group, to buy the house but the owner refused. We feel lucky to have even been able to sell our home at a break-even price to an organization that ran group homes for retarded adults.
The condo in which we now live was found to have a meth lab in one of the units. We were able to correct the situation immediately upon discovery and recovered the costs of decontaminating the area.