Just to clarify some things:
1) What I want to do is create apps that scratch itches I've had for years, and they're all outside of work, and even if there was something available off the shelf, I'd kind of like to be able to hack on it (have source), just for practicality and fun's sake.
2) I don't want these apps to be restricted to any one platform.
3) I never plan to monetize these apps.
You're right - if I was going in this to make money, it's a simple decision. Pitted against my time and potential revenue, a Mac + Developer Program is dirt cheap.
OTOH, I develop in Emacs and Linux for a reason, even when I'm developing software for Windows. Since investing in a Mac + Developer Program would be a net loss by definition, I'm looking for any way to still be able to make these apps available for iOS. Looks like Apple doesn't want that kind of hobbyist input to their ecosystem (and yes, while I'm a professional in that I get paid for same at the day job, I consider these apps as hobby projects).