>our community is just as massive as yours

That's just patently untrue. I don't think you fully understand the scale of OpenStreetMap. But the size of our communities isn't the issue, so let's set that aside.

>no one has ever told me why lollipopping is bad

1. It's topologically incorrect. Maybe start by reading up on the mathematical concept of Topology. Start with https://a.co/d/0MCqej0.
2. It doesn't accurately describe what is on the ground. It is often some arbitrary stem that meanders from the fairway to the inner feature it is describing, but that path doesn't "map what's on the ground",  a fundamental concept in OSM.
3. The gap that defines the stem of the lollipop is randomly wide and there are blades of grass in that area that are wrongly excluded from the definition of "fairway".
4. Just because it doesn't "break" OSM, doesn't mean it is wrong. I could define a road, but every single segment of the road is a new way so a curve would be made up of dozens of new ways. It wouldn't break OSM, but it isn't correct.
5. I could go on, but it seems like an argument meant to distract from the main point that rules and best practices exist and need to be followed.

Leniency breeds laziness. Things don't get fixed if they are allowed to lay fallow. Bad habits have been allowed to propagate for years now and it has created a MASSIVE amount of needed cleanup. We can't let these go any longer or we'll never get to a good state. When Alice is allowed to create bad data, Bob looks it and thinks, "oh, that's how you map that situation". And now we have twice as much to clean up than if we nipped it in the bud when Alice first made the error.

The terms of service don't specify how to map. You'll find that in the wiki pages.