@Shane Dennisonis your end goal just to find off market deals to buy for yourself? 

I understand that it may take time to build the capital for larger deals, but I’m committed to making it happen.

I would not sell unless you have another place to move that is basically paid for.

Usually, we keep the renewal to a discount to market rent to incentive people to stay and not incur vacancy and turnover costs, but that discount depends on many factors. - How good of a tenant are they?

Would it be helpful to you as a landlord have have not only the day to day automated but also have guidelines and quick access to local regulations (where there is constant change) in your assets markets to help you stay compliant and avoid potential lawsuits/fines?  

Management has to allow you to STR, and not change their minds in the future.

Welcome to the forum Edward!

We would bring in compensation to make it worth it too him and he seems to be open to the idea as long as we can figure out a way to do it without too much penalty on his side.

With today's market I think it's important to get creative with sourcing/structuring deals in order to make them strong investments.

looking to rehab on a property soon