Doing a deal like this is not a test the water situation you can just walk away from it when it gets tough, or when you grow tired of it.

I have multiple people ready to fill it every time a mid-term lease ends.

Have any of you encountered similar situations in your real estate investing journey?

I am just reaching out to see if someone more experienced would be willing to give me advice about if they think my plan is the best course of action for me and/or what they would do in my situation as for next steps after it has been implemented.

I can't say I am worried he is going to destroy the property as he does not seem angry with the situation however I am curious what those with more experience my offer in advice. 

We own multiple rental portfolios, manage our own properties, and always looking for new investments.

I soon realized that the best way is to just get multiple estimates.

There was an ad about a bank that lets you set up multiple accounts within the same business account, so you could set up one for each property you own but only have one login, etc.

That's what's risky about it.Also, what is the situation of the seller?

They have resources and networking opportunities with many in your situation.