If you don't have them, one "just in case" HVAC system can cause renter strife, mortgage lates, credit hurt, and a roof could just bankrupt you.

Without an eviction proceeding and the Sheriff on site to forcibly remove tenants and their property, you are stuck writing letters,asking them nicely, waiting, praying, hiring someone to help.Used to work for a company that had issues with squatters and in particular, a certain tenant who intentionally screwed the company by forcing us to file an eviction, and then proving we (or rather the attorneys) processed it wrong, and then causing us to start over...

A Handy man can repair and paint in short amount of time..It's a shock when you see damage caused by a tenant, but it's part of the business...

Let's say there are tenant-damaged items, the home is messy, the weeds or 4' tall or whatever condition caused by the tenant that interferes with its showability in getting the property rented.To help avoid this, can we require, as in legally defensible in court require,  that the tenant needs to have the house in rentable condition at the time they give their 60-day notice, and if they don't we can make the repairs asap and charge them instead of giving them until their move-out day to repair the items themselves?

I just read the Florida Statutes and it says that I am responsible for any damage to tenants property if it is caused by my non-compliance to maintain the unit.

My credit score is fine (760-780) it's just not being able to show proof of income since I was transitioning out of previous business endeavors for the past two years that's causing an issue and ultimately leaving me in the dark on how to utilize the BRRRR strategy now.

Your lease should say the tenant must pay HOA fines for problems caused by the tenant.

I don't mind guaranteeing the loan (I have a great credit score and zero debt) but I have no proof of income to provide and this is ultimately what's causing an issue with me doing the BRRRR strategy since I need to be able to get lending and then cash out refinance at some point. 

Is it causing prices to go up like foreign investments are running up the values in Chicago?

Cause Charles is right, it's not easy to find a deal there.