First let me say that I really like HB and when I first started using it a few years ago it just clicked with me much better than the others I had tried.
Here is some of what I would like to see in some future version.
I use the Ocelot for IR and I would like the ability to tell it which zone to send the IR command out through. Right now you have to specify the zone when you learn the IR command but I have 2 of the same device that I need to put on two different zones and the way it is right now I have to learn all the commands twice.
Better WinAmp integration and a better playlist control with repeat and shuffle.
A client server setup so that I could have HB server run as a service. I know that I can auto login my server machine but I would rather not have to plus I would like to use the client on my desktop machine without have to remote into the server.
Nested If statements in tasks and more conditions.
I'm sure I will think of more later.