Steam running linux and wine at the same time
Now is posible to connect two clients, e.g. Linux-native and Wined-steam, in same machine in same os.
The dual login is now possible because of Steam Home Streaming feature, the restriction login changes and life goes easier for us.
http://store.steampowered.com/streaming/
START STREAMING TODAY 1 Log into Steam on your Windows* PC 2 Log into Steam on another computer on the same network 3 Visit your Steam library to start streaming between them
*NOTE: IDK if Mac users can use this feature, but Linux user can use Home Streaming, i use it daily the webpage is outdated (10/22/2014).
Even if it could be technically possible, you can't be logged on the same Steam account at the same time in two different clients, and I imagine that you wouldn't have two accounts with games split around.
Running games on wine would also be game-dependant more than steam-dependant since each game has it's own requirements and prerequisites, therefore some might work, some might not. A better solution would be running dual boot, or a virtual machine, with both linux and windows, but I wouldn't rely on a virtual machine's performance.