1. I am only impersonating the one user for the app ( the one i set in the web.config ). If I am doing this, should I be OK with the pooling? How can I tell - is there somewhere in the OS that will show me my connection pool?

2. I have the user on both machines and the connection to the db does not seem to be working. I think what you are suggesting is:
On the db server, if db1/webuser has authority to the database, then ws1/webuser running the asp.net app should be able to connect to the database. Is that what you are indicating?

Thanks in advance for your always insightful advice.