John,
It sounds like you are fighting on a lot of fronts all at the same time. This is a common thing when moving into .NET development...and when you add web on top of it things can become more frustrating.
We all have preferences as it relates to languages and though I totally know C# and love the language, I have come to appreciate VB.NET over the years for application development. I have also noticed that most developers have an easier time moving into VB.NET versus C# when coming from any background other than C++...so that is why you see VB.NET as a base many times. However, this is really somewhat irrelavant in regards to trying to create a prototype application.
The first thing I would do is load VS2008...much better all the way around and this way you are not running to catch up. You can also run any of your existing .NET application in this environment without changing any code...it supports .NET 2.0, .NET 3.0, and .NET 3.5. This will also make it easier for you when you start looking at our new samples...they will all be VS2008 projects. I don't even have VS2005 on my daily development machine any longer, just test and Virtual Machines. Most of our current samples are VS2005 solutions that can be upgraded to VS2008, but all new samples with be VS2008...and it makes it easier when everyone is on the same playing field.
Next, you should first create a simple WinForms application so that you can see how the BOs, etc. work and interact. Then use those same BOs and create the same form on the ASP.NET side. We have a new sample application that we are working on called StrataFlix that does this very thing, but since it isn't ready it doesn't do us much good today 
Finally, I want to help...that is why we are here and what we try to do with all of our developers, but I am not sure where to start here. I was going to create a quick sample in C# for you that loaded a ListView from a BO so that you would have something else to look at past the sample that you already have (which does this by the way and is a separate control that using the grid and a WBBS).
Sorry for the ambiguos response, but I hope that his might get us going down the right path.