The first thing I did was go to the bar because I was under the impression that these games were all about finding clues in the bar. I didn't back out when I chose to enter the bar because I didn't want to stop halfway. I didn't dare to choose too crazy an option in this game because the background setting was cowboys and it could have killed me, so I always followed the instructions strictly. I really like the ability to enter town names at the beginning, will this appear afterward?
Now for the game as a whole, I have a guess that the cowboy is the main character, the man in black is a vampire, and the man in gray and the old woman look like they are in cahoots (I think they are bad and wanna cheat on me!). I saw your description and it would be great if I could be a vampire too! It's kind of like the "New Game+” setting of some games. Looking forward to your story development!:D