Your progress is good and I admire you making this thread. It's ballsy but you seem to be pretty ballsy too. I look forward to seeing this continue.
One thing you might wanna' do is sprinkle some variety in there. 30 days of the same venues and places might bore you into de-motivation. Grab some buddies and hit up a new City, find a loser friend and try and wing him in a night out (obviously pulling at the same time). One game I play with friends out of boredom is "Stag Party", which I think you guys called "Bachelor Party". One guy gets nominated as The Stag and then you act as if you were on his Bachelor Party, wearing either themed outfits (suits, fancy dress, same colours etc) and it basically gives you free licence to talk to strangers. People strike up conversations with you and on top of that you can play games, "the stag has to get a photo with five redheads" etc.
Best thing is, alternate where you go and you can have a different Stag every night of the week. Would be fun to write and read about too.
Anyway, all the best with the rest of the challenge. Can't wait to see the rest :)
Thanks for the motivation and idea bro ;)
Start up a challenge or journal and you got yourself a follower