was the ACA "doughnut hole" specifically calculated to...

[gratuitous]

9. Complicated legislation always needs amendments and tweaks

Often, the problems in legislation don't become apparent until they go into real world application. That's why there is a mechanism to amend legislation and plug holes. One of the first problems that cropped up with the ACA was the challenge by its opponents to mandatory Medicare expansion. The Supreme Court agreed that the Act had overreached in requiring states to accept Medicare expansion. Who wouldn't want free money to help a state's citizens be healthier? Plenty of states, as it turns out. Each and every one of them controlled by Republicans. Once the problems became apparent, it was the Republican-controlled Congress that refused to do anything to help Americans.

So yes, there were problems with the ACA. Whose fingerprints are all over those problems? Republicans. If your friend is totally against Obamacare, make sure he's mad at the people who have worked so hard to hurt him, not the ones who tried to help him.