The leak damaged the flooring and fixing the issue may result up to $10K in expenses.

I also discovered damage to the roof and had to replace that, plus I graded and graveled the driveway and parking area. $24,000 worth of improvements, $20,000 in lost rent. 

A misdemeanor may be sufficient to deny application if the conviction was recent and didn't involve a more serious crime, such as battery or intentional property damage.

Are there alternative ways to do this that are more hands free for me but still effective? 

This will keep you personally protected and allow you to run your real estate business far more effectively.

Should I have the agent send three separate offers, or is it more effective to choose one offer and include a letter that outlines the other options?

I have also had a lot of seller's this year and every single one of them was willing to offer 2.5% to the buyer's agent and did not want to wait till the change goes into effect to list.  

For example, both of the following are possible: 1) Extreme leverage - an "All-in" bet on appreciation: A syndicator can raise capital for multifamily, take out bridge debt on a low-cap rate property, and then lever up again with preferred equity to effectively give the common equity a 90%+ leverage.

Hi all,I had a tenant move out leaving over $5k in damages. 

What damage could it possibly cause that their security deposit wouldn't be able to handle, worst case scenario?