Some lucky ones spent as little as $4k on FSD? (Can't remember the low water mark, their autonomous driving schemes have undergone many sales revisions.) IIRC FSD was never transferable, except Tesla occasionally did carve-outs to juice select new vehicle sales.
Whatever happened to Elon suggesting he would raise FSD pricing into the mid 5 figures because that's how valuable robotaxis are to their owners? But yeah charging just $99 monthly for FSD seems like a big fuck you to the paying beta testers. Unless it's just a temporary ploy for marketing (and even then), it doesn't seem to make sense.
How we should feel about people falling for obvious cons really depends on the con and the victims. For example, we should have sympathy for people who get wrecked by (used) auto loans at usury rates even if they're flunking the very basics of personal finance.