Rikki, I hope somewhere in your setup you are using effects such as reverb & chorus. If not one of the best places would be in forte Ensemble. There are free effects available on the internet. I use the Sonitus effects which come with Cakewalk Sonar. Equalizers are also helpful.
Scott, if you carefully study midi and its various ports you will find most of your issues with Live - Styler or OMB will disappear. You are in the early stages of this. It won't be long and you will be an expert. In addition, a little knowledge of sending program change numbers and effects will also go a long way to making your system work and sound good.