First thought was the two girls went downstairs to get into their Santa presents and could not find normal music that late at night. 

Asking for POF (lender pre-approval, bank statement, line of credit etc) for a property like you have is perfectly normal. 

This is a vacation spot that I normally visit several times a year and the short term rental income will help offset the costs. 

You could argue tenant never made you aware of the leak so it’s on them but normally that doesn’t get you anywhere.

That might be normal and expected in IL.

So on Fridays he would take a few complaint cards that came in about the Mac and Cheese and personally call the folks of course to hear him tell it was quite humorous calling ( normally a house wife) and explain NO I am the President of STauffer and I want to hear why or how we can improve our Mac and Cheese..

The problem is, economic contractions (recessions) are a normal market of a free market economy.

The General contractor must spend a certain amount of hours each week on each project that he is being an RMO for, and has liability for any construction errors or defects, even though he actually does not have as much control as he normally would. it's really a niche for older retired contractors, it would just be an overwhelming amount of work and potential liability for a younger GC.

Normally you need to find a bread and butter B class neighborhood to make money in real estate.

Normally the only time you get a number of repairs is during turnover.