But then again if there is a big tree leaning over that brand new roof, or if you often get significant hailstorms and the like then the equation may change and you would want to be setting aside more for expectable damages/treatments. 

NFL home-game weekends would be nice also.And the other end of the fun-misery spectrum, you have some of the world's leading cancer treatment centers just down the street, and so there are always people coming in from out of town for long periods of time for treatment. 

Could you shed a bit more light on the tax treatment of Schedule C vs E in this type of scenario?  

The difference between the two treatments is whether or not you pay the 15% self-employment tax on your profit.Still, I side with Ashish in recommending professional help, as my suggestion needs a more detailed discussion before implementing, with a few pitfalls to address. 

General advice is to avoid Quicken and Wells Fargo, Quicken is overpriced with fees and Wells Fargo has ethics issues.

JohnsonIt is against the REALTOR® code of ethics to get between a client and their agent.

He told his doctors that he didn't want any more medication or treatments and will no longer be seeing them. 

Your absolutely right though, need to get that termite bond and ongoing preventative treatments.

Once you find a good sub he or she can refer you to different subs with good work ethics.

There isn’t really an issue with you investing and also practicing RE in your home state as along as you abide by the ethics and standards you pledge to uphold when applying for you RE license.