The big problem with a purely web-based approach is that everyone *has* to have an internet connection. There are still many gaming venues, especially large Cons, where internet access is unavailable, horribly slow, and/or expensive. So a purely web-based model is hamstrung out of the gate due to this limitation. We're using a hybrid approach with our upcoming Realm Works product, and we're looking at hybrid solutions for future use with Hero Lab as well.
So go ahead with the iPad version, but for those of us who DO have internet wherever we go (most of us in our pocket) - any way you could at least implement some sort of API to request information from the HL running on a PC? Then the community could develop the web page's to display, and feedback updates to said data?