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I've tried everything I can think of.

the management app is able to connect to my smtp server, and I've tried to hit it by name, and ip, with and without credentials.

I've setup my smtp settings in the brand and in the departments.

However, no mail seems to be flowing from my site.

In the past, I've used "localhost" as my mail server from within web applications, and have had not problems.  that does not work for this application either

Look in the SMTP logs. Do you see the SMTP connections?

In addition to what Strajk said I would check SmarterTrack's log files as well. We record basic information SMTP connections and event have an error log that tracks exceptions in the application. If these show anything strange please let us know or send a ticket to our sales department. (sales @ smartertools.com)

Here is the entirety of my smtp.log

2009.05.20-Smtp.log

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13:38:11 Starting SMTP Service
17:18:04 Starting SMTP Service

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Are you running in a shared environment or do you have a dedicated box with SmarterTrack installed?

 Running shared. Everything else works great

We've seen customers with similar issues before. What we found in their setups is that their hosting company was not giving enough permissions to the network services user on their box. I would check with your hosting company to make sure your network services user has proper permissions over the SmarterTrack site.

Also, while you're at it... it would'nt hurt to make sure your site is running in Full Trust mode in IIS.

Another thing to check would be to see if the IUSR account on the server has read/execute permissions on the web.config file.