And since I can't really control there time I'll just set the standards of making sure everything is complete up to standards on the deadline. 

My proposal was submitted on the May 16th deadline and interview and selection was supposed to happen by August....

Unfortunately the dumbass governor just extended the deadline to August 1st.

We sent a lease renewal 90 days out and give them a deadline of 60 days out to inform us if they are staying or leaving and to sign a new lease.

Not only that, the seller informed me that they made a partial tax payment a few days ago and plan on catching up before the March deadline.

We will be very happy to see them leave, since the relationship has deteriorated completely since they moved in.However, we are a bit worried that if they cannot move out by Aug 31 (they are building a house and the builder is supposed to be done by Aug 15, but deadlines are not met sometimes in construction...) then they will say that the Aug 31 was a typo and per the contract the notice should be effective by end of September.

I also can't imagine her continuing to push out deadlines over and over again.  

Does he have a problem with any deadline penalty (as most small contracts drag their feet if they get busy) and if so, what would be acceptable to ensure a turn key build on time?

Then we paid the back taxes 2 days before the deadline.

I likely won it because I made a cash offer with a short deadline.