On June 7th, we sent an itemized list of deductions via text; he responded on June 8th, disagreeing and threatening legal action.

If so, it would make sense to figure that out first before deciding on a specific area.

figuring that if I track and work towards creating and "presenting" 250 specific deals to my clients.My Theory being: Tracking "deals presented" will pull forward the need to go search and find deals, and will also drive the deals closed and revenue numbers, so we shall see but logics out to me so I'm liking it so far.

Give proper legal notice of non-renewal and get them both out.

I know our lease agreement specifically states that if a tenant reports a maintenance issue that ends up not being an issue at all it's the tenant's responsibility.  

Well even if the rent is equal to the mortgage, you'll still be in the negative after repairs, CapEx, vacancy, etc.Why would you specifically be thinking of investing at a negative cash flow?

I recommend legal advice from an attorney.

I would like to do some research on other rental properties before I set my priceComputer algorithms are good for studying a general market, maybe even a neighborhood, but they are terrible for evaluating a specific rental.

Do not rely on it for legal advice.

If you need financial help, ask under the "Finance, Tax, and Legal" forum.