The other problem is his Social Security can become taxable.A JK Lasser publication covered it perfectly:"The special capital gain rates are supposed to allow taxpayers to pay less tax on these gains than on ordinary income.

From a financial viewpoint it can make perfect sense.

Gotcha, that makes perfect sense to me.

The handy tenant wanted to replace the well pump, the front door, and many other items in the house that were perfectly fine.  

Also, when you plan on retiring you want to have something to do every so often - and this sounds like perfect to me.

I have had carpet look like this and turn out looking perfect after a professional steam cleaning.

In a perfect world yes the court could tell them to pay, but if they don’t have the money, then it’s not worth the time in my opinion.

Who can provide data to anyone who asked, whether a court, an inspector, a tenant, a money lender, or whatever,  you will have it ready for them in seconds and it will be organized, and it will be perfect, and they will look at you as someone who they will listen too and take seriously.If you think being a Landlord is a Hobby whether you have one property or 100, you better think twice about that.YOU are responsible for the neighborhood, (depreciation of it, it's safety) and you are responsible for the people who live there, in your home, to have a safe and comfortable experience while they rent from you.YOU have more responsibility than most other Industries. 

I purchased landscaping bricks to go around the home, put mulch in the flower beds, removed a ton of debris (old roots and stumps) from the flower beds and manicured the yard to perfection.

@Phillip Johnson - Roy said it perfectly!