Damage and breaking a lease

[Hark Tukay]

Our tenants of 7 years are moving out next. They have asked to break the lease with 11 months remaining. When I went over to prepare for a showing I noticed there was water damage on the ceiling and a bunch of tiles are busted in the kitchen. None of the damage was reported to me. I know from previous damage that no one sells replacement titles that match. They have pictures everywhere including all the way up the stairwell. My questions are:

1) should I charge them anything to break the lease?

2) are they responsible for the damage due to negligence?

3) since I cannot replace the broken tiles can I charge them to fully replace the kitchen floor?,

4) can I charge them for the nail hole fixes?

5) What is customary for painting, etc before a new tenant moves in? Is it just understood that the new renters will have walls with holes or is there an expectation that all of that is fixed?

I believe the damages will be more than the security deposit. Do I just need to notify them of the additional charges as part of their checkout? Property is in VA if that matters.

Thanks!!!