Fresh cracked makes all the difference. Excellent finish to most dishes. The crap sitting ground up in a container for years? Yeah, that is bland as shit and shouldn't be a staple everywhere. I bring my own mini pepper mill most places. Pretentious? Maybe, but I don't really care. I just enjoy the enhanced flavor.

Depends on what you're making. There's nothing worse than under seasoned dishes. Freshly ground black pepper is a versatile ingredient that compliments many other flavors, but it's hardly a requirement for everything. I keep two spice mills on the counter, one with black peppercorns, and the other with white, because there's many things that can benefit from one or the other.

Since it doesn't have much "character" of its own, it goes well with many kinds of foods while also being generally agreeable to most people's tastes. That's probably the main reason it's so popular.

I don't care for it either, but it's fine if you also add salt

If it's like the only spice, then it's better than nothing, IMO.