I don't really have an opinion on how fast to move up, except I don't necessarily want to stick around if the next few seasons are going to be futile. I don't really want to stay in DIII forever, so it does matter to me if I'm not going to have good teams the next few seasons.
But again the other concern for me is, will my reputation take a big hit if I jump after one season (assuming I don't muck it up, and my senior heavy team does reasonably well)? If so, maybe it's best to try to grab as many juco players and mix and match the next few seasons.
I guess it's plan A or B.
Plan A is to un-redshirt the other guard (who will likely start at pg) and go for as many wins as possible this year, with the intent to jump.
Plan B is to keep him redshirted, maybe take a slight hit in terms of team effectiveness this year, but keep him around for one more year, and try to bring in as many juco players as possible for the next 2 seasons, in an effort to avoid bottoming out.
Plan C is not something I want to do, but would include re-building through a mix of a couple freshmen this year, and then mixing in juco players in the next few seasons. That's what I'd do if I was at my final destination and was trying to build a long-term winner. But again, I don't really want to stick in DIII all that long, I'm thinking more like 1-3 seasons.
I appreciate any thoughts here.