I wouldn't worry so much about your actors and directors.  Actors will show up because they want to act and directors will show up because they want to direct.

 

So your real - and only important - question here is what do your patrons want? 

 

I think if you did a season of Simon, it would be important to vary the type of show.  You don't want to put Odd Couple back-to-back with Barefoot in the Park back-to-back with The Sunshine Boys.  All of these shows are of a similar type of Simon.

 

Open with a strong comedy (ie: Barefoot, Female Odd Couple, Rumors), then do something more dramatic (ie: Gingerbread Lady or Prisoner of 2nd Ave), then give them something not so well known (The Dinner Party, Fools or God's Favorite), and then end with something nostalgic (ie: Brighton Beach or Lost in Yonkers) and I think you could end up with a very financially successful season that will have wonderful parts for a variety of actors and will give directors a wide variety of creative opportunities.