2 ps worth -
The future feels very strong right now. All the recent happenings like the Milan reports and interviews have been really impressive. I get the clear impression that basenotes is well known and thought to be important within the industry as well as among the hundreds of thousands of readers.
My advice would be - do few things well and always look after the core of what basenotes is first (directory, community, editorial), after all, those are what put value in the advertising.
That said, there are times where one needs to take a punt - risk things and expand (take on staff??). Make sure that it is clear how this will pay for itself in the long run before you start. Bussiness plans are good...could be worth taking a few days out to write one?