The landlord has 21 days to send you a itemized damage list and the remaining deposit.

Make sure you aren't in a rent controlled area or that your tenant is not section 8.Enforce items in the agreement that you've been lax on.

I am not sure if there is any more downside to any of the items you already listed.

Given the roof and maintenance issues, you may not want to rush into these without thorough due diligence just to save on taxes - capital items could potentially eat away any tax savings.  

They are issuing title insurance on the property, but I dont see how you can insure the title without those 2 items.

I am not dead set on one of my options so if you have any creative ways you have saved money on any of the above items please let me know.

Especially if the the large items like Roof, HVAC, Hot water were replaced.  

Each item has a point value, and whoever has the most points is my top candidate.  

I would like to redeem it, have contacted the tax collector's office and they gave me a affidavit to be signed by the owner of the tax lien.

For your current tenants, you might want to notify them certain items such as drain related issues are their responsibility after they move in etc, and modify your lease for new tenants as well.