My years of life experience and business experience prior to investing in RE actually became an asset when interacting with tenants and managing the business.

If I recall correctly, if you pay off the debt within your IRA more than 12 months prior to the sale of the property, then there is no tax on the gain.  

However, if the maintenance issue is an bigger one, I usually need to make several trips: Check it out myself first, meet someone to get an estimate, check progress of work if it is over multiple days, review final work, etc. prior to paying for the services.

Prior to me calling him, he was in the middle of getting the property appraised externally to be re-financed by bank.  

You might try making your purchase offer on a place contingent on having the roof be properly repaired prior to purchase.

As real estate investors, we have a very unique set of needs and most companies and agents out there are limited in their ability to structure things properly and even offer the right coverage in many cases.One thing everyone needs to understand is that anything having to do with rental or any other form of passive/residual income, is considered a business exposure and absolutely needs to be separated from any of your "personal" activities.I've been in the insurance business for 11 years and as an independent agent prior to becoming a real estate investor, I made this mistake all the time because I simply did not know, and most don't. 

I have a couple of small upgrades prior to renting (paint, new baseboards, etc) that I will definitely have to factor in. 

(So look to their latest 'market cycle' schemes, media hype, 'fear mongering' tactics, and the prior 'bank panics' to 'stock market' and 'real estate' crashes... particularly over the past century.

I think this is a somewhat unusual question as I searched and wasn't able to find a specific answer.I found a boarded property that just recently transferred ownership from the prior owner to Fannie Mae, the deed appears that it was a foreclosure and recorded just a month ago.  

Prior to acquiring a property, I am 95% certain of the cash flow I can produce...that is not speculation.