I may however discuss collecting for the pet damage now but not fixing those items until they move out to avoid them having to repair the same items again since the pet damage is likely to reoccur. 

I'd follow landlord/tenant laws regarding itemization of damages and return of security deposit, including a bill for damages exceeding the deposit. 

@Brandon Morgan, one other item to consider if you're making long-term plays:Property in Puerto Rico is not considered "domestic U.S. real estate" for purposes of 1031 exchanges (unlike the U.S.

Not a CPA or tax professional.I’ve never audited every single line item of my S-Corp tax returns for over 18 years, and I’m truly curious why it really matters in one years instance, what corporate account was used to conduct business, as long as the financial information is accurate and correctly reported from said dedicated business account.This should be a separate issue from proper and legally correct business operations, ie a checking account with correct tax ID, no outside commingling of funds with self or other business entity.

It's not as much as you think and will save you tons in the end because they make it much easier for the bookkeeper to do their job and categorize items correctly so that when you send your files to your CPA there is little to do and everything was already optimized by the CFO to capture the best tax write-offs PLUS you've made the best trade-offs.  

Mainly because the essential repairs were standard safety items, or necessary cosmetic updates.

You could add a clause in the lease stating the penalty for late payment.I like the idea of electronic locks.I would identify the items that need updating and plan accordingly; roof, furnace, etc.

He had to take out financing to pay for larger capex items.

If questionable or major items needed, we wait.

There is a big difference.Social Services to me means section 8 housing vouchers, food stamp existant, and other welfare benefits.Social Security (whether you agree with the program or not) is based on repayment of money you earned while working and supposedly placed into a trust for retirement.