On my old street we had them for six or seven years in a row, precisely as you describe except that our neighborhood was neatly bordered by four major streets so we just invited everybody within that border. We usually had over 100 people, one year it was close to 150 (The woman who lived directly next to me was an obsessive counter of things, it was both sweet and useful to receive her yearly reports on all the various data involved. She does this for everything: she counts the number of trick-or-treaters she gets each year! She explained that this was how she knew how much candy to buy. For someone like me, it was kind of like living next-door to a visiting alien. But a super nice one that was incredibly kind to me through the years.)
I didn’t have any of the social issues or need to not know my neighbors. I liked my neighbors and it was fun to meet people and hang out.
But there was really only one reason that I personally loved the block parties and looked forward to them eagerly every year, a reason which was both fun and a nice ego trip for me: I was the DJ, and I basked in the raves that I received.
But it wasn’t like I was standing there picking the tunes “live”, as it were, making it obvious that I was the one responsible and rendering the compliments I received easily dismissed as polite, oh no: Every year I spent weeks putting together the playlists so I could just flip a switch and the music played for the next five hours, very carefully (and gleefully) curated to match what I already knew would be the mood changes and activities over the course of the evening.
People would seek me out to tell me how much they loved the music and to ask for CDs. I received AAA reviews from the little kids to the grandmothers, which was what I was deliberately seeking and hoping to achieve, making it extremely satisfying.
And that’s kind of a thing for me; I get asked to “do the music” for weddings, block parties, and most meaningfully, one memorial (so far). In that case, the music was coupled with a video of photos of the deceased, which of course I also put together. (It may seem weird, but that might be one of the things I’m proudest of creating in my life. On the one hand it was really well done, if I do say so myself and here I am saying exactly that; it was just as good as I hoped it could be, creatively speaking, which is saying a lot given that I pretty much didn’t sleep for about 72 hours and arrived at the memorial at the very last possible minute in a nearly hallucinatory state. More importantly, the people he was closest to, his wife and his sister, were effusive in expressing their praise and their gratitude. The fact of they asked me to do it to begin with was an incredible honor and its own form of praise for my skills in this regard.)
But back to the block party music: I loved finding arresting songs from each of the last 9 or 10 decades, since our guests included people born in each of them, mixing the familiar and beloved with the semi-obscure but brilliant, finding amazing covers of extremely well known tunes (Chris Cornell’s Billie Jean always stopped people in their tracks) And the thing I probably loved most was coming up with unexpected segues that somehow just worked: Sinatra flowing into Metallica, Jesse Cook side-by-side with KC and the Sunshine Band, Cab Calloway next to Panic at the Disco, Betty LaVette to Sufjan Stevens to Led Zeppelin… it was a total blast and I miss it.
So does that over-answer your question? 
