Hi Scott,
I am not 100% sure what you want, but the CSS can route trafic, no problem.
If you have the CSS on a kind of public DMZ, and here is the VIP of the CSS. The ASA does a staic nat from outside to this DMZ.
The server(s) is on another DMZ and they route (default GW) from servers to the curcet ip of the CSS.
Outbound trafic from serves can be done on more than one way. here is a option.
The VIP can be running on port so (443 and 80), the rest of the outbound trafic can go routed by the CSS so you will see the CSS Curcet address on that.
If this is not what you want pls. tell or send a picture with some info
/Soren