It definitely can be a chore.
I organized a large (600+-person at its peak) Meetup in Park Slope, Brooklyn, NY during Meetup's hayday (2010-ish).
Meeting heaps of different people from all walks of life was interesting at first. But like a previous poster stated, connections like these are fleeting and take a lot of work to maintain (especially if you're a man, which I am; see the end of this post for more on that).
Consequently, the process of meeting people eventually became very same-y after a short while, and knowing that these conversations usually won't amount to anything other than nice, fleeting moments got old.
There was also the drama of managing "interesting" personalities in a free Meetup group. I passed the baton in 2012 or so, but that's another post for another day.
I'll conclude this post with some unsolicited advice: try to learn what people do for work without asking them directly.
EVERYONE expects this question, and it can be a conversation killer if your occupations don't intersect (less likely) or if the person you're conversing with hates their job (more likely). Everyone ALSO loves talking about themselves. Finding out how someone spends the largest part of their day without asking point-blank adds interesting twists and turns that can really liven up a conversation. It also makes you a better listener and better at asking questions.
I lied; I have more unsolicited advice. The easiest way to give a shit about what someone does for work is to ask lots of questions! Unless they hate their job, in which case, you'll want to ask questions that get them talking about what they do enjoy!
Typing that last paragraph reminded me of another reason why I got burned out on socializing with people. I'm a man. Most men only like sports and video games; two things I couldn't care less about. Socializing with other men as a man who dislikes these things is extremely difficult, especially in the US South, where I live. I blame the suburban lifestyle, but that, too, is another post for another day.