Greetings from Chicago. I have been leatherworking for almost a year now and have finally gotten to the point where I am investing in better tools. I got started because I was too cheap to buy a nice leather watchband and thought I could do better myself (and have spares). Well, I don't know if I like my watchbands yet, but my wallets and bags are coming along nicely. While I am not ready to start selling my bags (I still make mistakes), I have sold a design to someone interested in manufacturing it and have requests to start doing custom work. I work full-time so my goal is to sell enough goods to continue to make goods - a self-funded hobby.
Prior to this I was big into headphone audio and watches, but have sold off quite a bit to fund leatherworking.