Many of them become entitled and create problems, particularly for amateur landlords that don't know how to manage well. 

Quote from @Timothy Rei: The absolute best way to solve this problem would be to offer the teacher $30~$60 to cover the cost of keeping the heater on during days when the room temperature fall below an agreed upon threshold. 

Unfortunately, this problem waste a lot of my time that could be spent on other investments.I have used the same tax professional for many years and he is very educated, but also much older than me and it's hard for me to understand all the reasons he has expressed why is better to put the rental on my personal tax returns.

What problems do you want to be solving?

I’ve been considering working for as a acquisition manager for a  wholesaling company, as I believe it would help me develop skills in property analysis and enhance my sales abilities.

Reverse 1031 Exchanges are more complicated and have higher costs, but can solve these problems. 

No way is this a scheme to keep EM for the seller..Anytime I have had EMD disputes it usually gets solved with a 50 50 split since I know what will happen.. what happens is exactly as you describe.. money is to small to realistically hire an attorney to collect..

Direct booking website, highly attentive to guests needs and experiences and consistently enhance the property during ownership.

I thought I could solve the vagrant problem by buying and repairing the buildings.

First of all, what a great problem to have!