By new to VB, do you mean that you are new to programming in general?
Yes, one could probably create a program to do what you describe. and since you are new to VB I would say yes it could prove to be difficult.
There are ready made alternatives that do what you say, for example I use Real player downloader to download, convert and load my iPod with videos. The version I have loaded does so without cost.
My advice for a new programmer would be to create something somewhat simpler than converting media. Perhaps you could create a project that plays audio files to start with.
Something like this
Media Player Class[
^] (This is in C# but uses the same methods as VB)
Hope this is helpful. Good luck, happy coding! :)