It needs fixed, and should be fixed, so taking $20k (completely random number) off the price, means you have $5k more in your pocket from down payment and $15k lower mortgage, which doesn't necessarily mean you will have the money to get it fixed.At the end of the day it is all business. 

Rent is paid at random times and one 4 weeks late.  

That has me worried.To put some random numbers to this: Say her death benefit was 300,000 and the current market value of the IRA/Annuity is 500,000.

After researching for several months I decided to just start cold calling home owners and getting my feet wet with having conversations with random homeowners.

Now it takes that long to get the paperwork filed, including 2 years tax returns, an appraisal scheduled & some random underwriter to tune in a month later with more mundane questions.

Knowing what you know about the property, would you buy it from a random seller for 27k? 

However, that is of course a question your market needs to answer for you, not some random opinion from the internet - he he.If you are going to pony up for a new floor and pulling the plywood is part of that, one option there is to go old-school classic mixed with modern technology.

I randomly stopped by Barnes and Noble the other day and found Josh and Brandon's book, "How to Invest in Real Estate".

OSHA can perform a random walk down of a residential home but they often will not.

If it was a family member's name or some random lawyer as trustee, that would make more sense.