I started taking an active interest in learning to evaluate ROI and cash flow, and creating my own exotic spreadsheets and algorithms laying out my own personal strategies. 

I'd consider finding a luxury Realtor and paying him for an evaluation of your home vs the others on the market.  

However, it can be very helpful in evaluating properties once you have identified them as targets.For example... very helpful to know when a property is owned free and clear, or, alternatively, when a property has liens that exceed its value.

I've been presented with an opportunity to invest in a 7 acre parcel on a mountain in NC, and need some help evaluating it. 10% annual return on the $175k initial investment, and 50% of the net proceeds of each lot sale (12-14 lots). 

Evaluating deals

Okay, I'm starting to wrap my mind around how to evaluate deals (buy and hold rental properties).

I do have criterea which I use to evaluate and both of these tenants are acceptable.

Prepare with YouTube videos, let them know you are coming to do a "preliminary evaluation of the problem" to "assess repairs and schedule vendors".

It helps that I use a very good tax professional that can determine the legal write offs and provide direction to reduce future taxes.Looking into paying the owed tax is at least worth evaluating as an option. 

In the past, I have adjusted the due date, set up 1099 type tenants on a quarterly payment schedule, requested (and received) 2-3 months rent in advance, sold the property via lease/option, etc.I get that the norm is rent due by the 1st, late fee accrues on the 6th, but this tenant's situation apparently doesn't fall into the normal category, so ask the question, then evaluate whether you can live with (and accommodate) the answer.Good luck!