@Andrew KatzIn this situation, you can either (a) continue dealing with the pain of having your tenants that pay late and violate your lease terms or (b) deal with the pain of turnover but the prospect of getting better tenants. 

If you push collections aggressively now, you could force them to dig in, stall, or even damage the unit out of spite.

There can be surprises and damage to the property. 

The damage was absolutely insane—it ended up being a complete gut job.

Granted, after 30 years the place is a pig sty, but if he goes quietly, no malicious damage, I would most likely return his damage in full. 

Relatively simple installation as no walls were damaged. 

The security deposit must be kept in escrow, but it belongs to the tenant until the PM have documentation allowing them to contractually use those funds for damages. 

In my limited understanding it seems like the aforementioned brick needs to be reattached.It is my belief that the damage to the lintels, bricks and the internal water damage is due to the roof.

The loan on this house is $1,200,000.I moved in to my new primary residence by the end of the month.Starting July, my original primary residence was available as a rental and was being shown to prospective tenants.My new tenants signed a lease that began a couple weeks after showing, in July.To calculate my primary residence mortgage interest deductions, i'm using the following formula:650,000 / 2 = $325000 loan from January to June1,200,000 / 2 = $600,000 loan from July to December$750,000 limit / (600,000+325000 total loan value)  = 0.81 multiplier(0.81 * $X first house interest) + (0.81 * $Y second house) = total interest payed i can deduct from my primary residencedoes this look correct?

You are also very susceptible to damage during storms.