If this is a problem tenant who continues breaking rules, that's something you can work on later but for right now you should do the right thing and look into this.

They are still at a discount to the 10 year treasury bond (i.e. market trends indicate they will continue to escalate).

with the current market micro & macro trends, our market is poised to continue to go up for the foreseeable future.

Seems like a liability as long as you continue to own this property.  

But he chose that one over the others because it was very user friendly (for our older managers) and it offered a 'Groups' function where we could add certain individuals to different projects.

Long term goal is to continue building my portfolio of investment properties. 

Here are thoughts on building strong vendor relationships:1.Timely Payments: Pay vendors promptly upon completion of work to maintain goodwill and encourage continued collaboration.2.Fair Pricing: Negotiate competitive rates without undercutting the value of their services.

It was a good moneymaker for me and I would love to continue short term renting.

Been slowly rehabbing my own primary residence and debating if I myself would want to rent it out or continue living in it.

They are rules of thumb we use to function day to day because the FACTS are too needlessly complicated to use to make every decision in life.