Options - collect full payment for the 3 months up front and lower the deposit to secure against damages only, require insurance.

Are landlords required to give photos to tenants of the areas of damages / lack of yardwork / etc or just an itemized list of the deductions?

You can often uncover major things with a little research before you view the property - Ages of appliances, HVAC system, foundation/cracks, plumbing leaks, small electrical things (bring an outlet tester), signs of previous leaks, termite damage etc.

You have NO leverage, no matter what he builds or does not build, except for the developer saving some money in legal fees and cutting down on mesne profits damages.

Today, I completed the home inspection and discovered several structural issues, including bowed brick walls and a damaged chimney.

Destroying the house calling board of health for tenant damages and literally every little thing creates huge expenses.

He says that the front door was damaged which he got repaired but there is some damage on the back side as well.

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. 

Older homes that aren’t elevated could suffer major damage when the next storm hits.Many expect market saturation in the coming months, as flippers are snapping up flood-damaged properties.

Now, I'm imaging a scenario when every one of these tenants move out that I'll be paying their entire security deposit + interest even if there are damages beyond normal wear and tear.