When is it time to leave a program and go to another program?

Being satisfied means different things to different people. To me, the fact that you are asking is telling...and its telling me that there are somethings you aren't satisfied with at your current position.

And that's not a bad thing....5 years is a good barometer of what the program, school, AD, facilities, talent level, success potential and your own personal satisfaction will be going forward. Any successful endeavor needs to be re-assessed on a regular basis.

I teach umpires to divide their career into 3 stages.....What was, What is, and What will be. The point of this exercise it to define the needed steps to get to where you feel your ultimate coaching goal will be. it seems you are at that crossroad...

What is your motivator?...is it championships, is it money, is it a Higher level, is it moving on to college coaching? All these things are the same in an umpiring career

and they all require movement on your part.

I would only advise that you make sure when you do your pro/con list that you make sure to weight the con side appropriately.....location from home, pay, job security, pressure to win all weigh differently to all of us...best of luck to you in your decision... 

Passion4baseball, I have been in this situation before.  I too had taken over a losing program, it hadn't had a winning record in over a decade or won a league championship in 20 yrs, and turned it into a winner.  For me here is where the decision came.  I truly believed that I took the program as far as I was going to take it.  Yeah, I could have won multiple league titles, made multiple playoff runs, etc. etc. etc. but I was never going to be able to compete for a section title with type of player that I had.  The other part of the decision came when looking at the of player I had.  I was coming from a low income are in which players did not put much thought into college or college athletics.  I wanted to the opportunity to produce college athletes that were ready to go out of HS.  Everything that I asked for I got at the job I am at now and I believe my move was well worth it.  You have to ask yourself.....Do you feel you can take the program in any further?

Are you a teacher?  If so, you have to understand that you will have to start the tenure process again.  That also means that you will be the first one RIFed it that school district has to reduce staff.  In my area, there are almost no teaching openings and so, that is a major gamble as most districts are having to cut back. 

Personally, I made a change and it was a great thing for me and my family.  I did so in a fit of anger.  Looking back, I am glad that I ended up where I am because this district has been so supportive of me and my family.  I live in this district and did so before I made the change.  It was not an easy move and the change was from one of the top programs in the state/country to one no one had heard of.  It was so much fun making this school a baseball powerhouse for our area.  That didn't come easily.  You have a lot to think about.