I think eventually, once I'm more experienced and confident in my ability, I'd like to run one of each... A DI, DII and DIII school... I would like to get schools that I enjoy to watch and/or are local to me... For instance, I live in Central New York (in Syracuse), and recently signed up for Buffalo St in Naismith, because I grew up watching them play. I couldn't care less about the schools playbooks, as I'd rather be in control of a school I like. As I read more though, I may avoid DI as I rather like the variety in recruiting and seeing the different teams than those on TV all the time. :P
I would, however, like to avoid Fastbreak stuff. I like the idea of Zone (Thanks Jim Boeheim), but I'm not unable to keep the defense in place.
The only time I see myself moving up, or around in a league would be to get in control of one of those types of teams. Once I have them, I doubt I'll move much... I don't mind spending a season or 2 rebuilding, if it helps set me up for the future.