@Chris MasonI'm failing to see how Johnny is in a better position for a mortgage... 

We haven't had garbage fines, it is the noise ones and we have language in the lease that the tenants pay all municipal fines for ordinance non-compliance and if they fail to do so we will pay and charge it back to the tenant, deducting from deposit if need be.

Hot water heaters, electrical work, AC failing - big problems.  

Failed to mention that to any of the buyers. 

They either give up too soon or when they do make money they fail to properly reinvest back into their business. 

Chrome’s cheap, but I’ve hit far too many challenges with things that should just work, like uploading folders or files over a certain size that simply fail, kicking me back to underpowered apps designed for a phone.

If the court orders a tenant to pay a certain amount and the tenant fails to do so, you might be able to finish the process and get the eviction.

I am a fervent believer that the market will dictate how/if his business will succeed or fail.

If the windows are failing, this can lead to further damage, especially ones near ground level.Paint is cheap and you can do that yourself. 

We (you) already know that a high percent of new businesses fail.