Platforms like Zillow or Redfin can give you insight into comparable properties, and PropStream is great for deeper analysis like liens or ownership history. 

So, what is happening today is not as important as what will happen in the foreseeable future.If rents are increasing faster than inflation (I use 5% per year as an average rate), then it may be worth holding the property, since your cash flow will increase as rents rise.However, in your post you stated, "Mortgage rates have kept increasing as well, that's why I put a range on negative cash flow."

Investment Info:Small multi-family (2-4 units) buy & hold investment.

You’ll need a real estate attorney experienced in creative financing.Land Trusts for Extra Protection – Many investors in Illinois use a land trust to hold title when doing subject-to deals.

I would find a loan officer that does both conventional and FHA renovation loans to compare which has better rates and terms for your situation.

They'll require that you fill out a bit more information, and even ask for a picture of you holding your driver's license next to your face to confirm your identity.

Most of the “deals” have no meat left on bone except for maybe a long term rental hold after repairs.They ironically sponsor a lot of the meet ups I’ve been too here in DFW. of course they do they live and breath on newbies..  

If you adhere strictly to the laws, you will be limited in the services you can offer to your relative compared to what they would get if they listed their property with a licensed agent, and they will get less money for their property working with you than if they hired an agent.

Having professionals we can call to see how backed up they might be factors in as well - if we can't get a roof done ASAP, that holds everything else up if we have a leak so again, more time, more holding costs, lower ROI.Unfortunately I do not think there is a magic metric that can tell you if the deal is a winner or not. 

I was holding approximately 20 of their properties at that time, so you can imagine that unexpectedly paying out 20 interest payments every month was impossible.