Couple thoughts -
I love how everyone thinks they know Flexibit's business plan. "Well they should just charge X." They know what they need to charge to continue making software and running a profitable business. We have no idea what their books look like.
I also love how we all spend THOUSANDS of dollars on Mac hardware and complain about being nickel and dimed for quality software. Quick back of the envelope math - I use Fantastical on $3000 worth of Apple hardware (macbook, iphone, ipad and watch). It's probably my most used app, and at $40/yr, that's a drop in bucket.
The price of Apple hardware doesn't correlate to a need to pay whatever price someone is dictating. Let me put it another way... Just because someone drives up in a BMW doesn't mean they should be charged more than someone in a Toyota. The two have vastly different starting prices, but there doesn't need to be a "he's loaded" assumption latched on here.
I have no issue paying for quality software. Hence why I paid for Fantastical in the first place (including on my Mac as well as my iPhone) and it wasn't a "cheap" app to buy. For users of the app their uses will vary quite a lot, but to me $50/y for a "viewer" app that is just a nicer way to see the stuff I'm already storing myself (I host my own Exchange server which is where my personal calendar sits and my work one sits on the company Exchange server) is a bit heavy. You get even more annoyance from users like myself when the V3 upgrade allows me to add attachments on my Mac to my calendar entries (which are again stored on my own server), but on my iPhone I get nagged to buy a sub to do it.
Even more critically, some of us watch our spending a bit more. I'd prefer not to commit to $2/m here, $5/m there, $20/m over yonder and before you know it I'm burning away hundreds of dollars a month on software and am constantly forced to decide "is this worth it
this month?". I find it much easier to approach it from the other way "I only want to spend $20 this month on apps which upgrades or new apps do I want to pick up?".
If I don't need an upgrade I can delay it. If I end up not using the app I can mothball it and not have another job managing subscriptions.
Especially when subscriptions now are all or nothing. Want to use the app? Pay up every month even if there is nothing added that you actually care about. It would be much more palatable if you at least were permanently entitled to the new features added during your subscription term...
But I digress. You seem more focused on the "he's loaded so he can pay up" side of the debate.