Agh. This thread is giving me a headache.
rapidrickc: new OSs work well on new machines. Old OSs don't work well on new machines, or not at all. Installing DOS or Win9x on your machine _might_ work, but you'll run into all kinds of problems. If you really, really want to use old OSs with full hardware support, get an old dedicated gaming machine. If you're going to get an old machine, keep your controllers. If you're going to use a new machine, sell the old shit and get something with USB connectors.
There is no "best" OS for DOSBox. It depends on what machine you're running, your knowledge level, your budget, etc. . In your case I'd suggest Windows 7. DOSBox will run nearly all DOS games. Most Win9x era games will work, a few will give you troubles, and a handfull won't work at all. For those you have to resort to additional techniques, like for example running them in a Virtual Machine.
Asking "which OS is best to run DOSBox" is like asking "what is the best car". The one possible answer to a question like that is "depends".