Just one random pain point for me: I often wish there was an easy way to find local events both in the city where I live and when I travel. Usually I have to try to find a local paper or two and then see if they have an event calendar, but it's not always successful, then it's also a matter of checking the visitor's center, chamber of commerce, etc. And of course there's social media, and lots of local businesses only post their events on their own feeds and not even their websites anymore :(
I wish there was a service that could scrap all these local papers and such and present a simple events view, with good filtering, that also point back to the original sources. I'd be happy to pay $5-$10/mo for this, if it were reliable.