How is it going?
I can't really help you with this one because whenever I made myself a bootable Linux USB drive, I meant to install the system on one of my computers once and for good. However, if something in Wine or DOSbox weren't going your way, I can lend a hand.
That being said, Wine is now really good at running Win things and most of them run straight out of the box, without needing to resort to obscure settings and hacks.
By the way, I wouldn't really bother even thinking about booting DOS. Just make a live Linux USB stick and install DOSBox alongside of Wine. They both do their work very well. Especially for the older games, they do it better than native systems. (An example to illustrate: I used to play Heroes II over LAN with my brother. I played at my Linux box, he used his Windows computer. Every 10 minutes or so, the connection dropped at his side. When I gave him another Linux box, we played for several hours without interruption, not mentioning that we had other goodies, for example real-time screencast from each box to the other.)