I'd say a better question would be; How many rental properties do you need to own before you decide you're a charity and not a business person? 

Hey @Charity Daniels yep - as long as you register for it, you'll get a replay link the next day! 

How about contacting several charity organizations and explain that this guy could use some help and is not physically able to work in his yard and around the house. 

I know this because I run a chapter of a charity (Sleep in Heavenly Peace) in my town that builds beds for kids that don’t have beds and Lowe’s has been an amazing partner, donating tools, lumber, and their time to help us building and deliver beds to these kids.

If I was looking for a tax break I would donate to charity  or increase my Ira contribution.

Donate to charity - church, habitat for humanity, nearby school.Let them go for unpaid real estate taxes.Craigslist ad offering free house.

I gave you a charity vote Will.

We’re not running charities and chances are, this tenant will be a problem tenant being late frequently.

What is the best way to transfer accumulated wealth to desired recipients (spouse, children, family and charities) to maximize the amount transferred, minimize the cost of that transfer (and planning) and perhaps minimizing taxes.Lots of people make no plans and Uncle Sam (and sometimes the state) end up being a major beneficiary of this wealth.

Another benefit of volunteering for non profit/charity events is the possibility of meeting private investors.