Having a charitable purpose, like providing afforadable housing, can be the basis of your 501c3 status that allows you to obtain tax deductable contributions in your community!

Has anyone ever donated land to a charitable organization before via 501(c)(3)?

If the purpose is the former, than you need to be honest about your motiviation, if the latter than any potential investors or lenders are interested in how you are going to make money - unless of course you are getting financing from a government or charitable organization whoose specific goals include social engineering.

It's really a matter of how charitable you want to be.

Consider sending mailers to charitable groups/churches: They frequently receive gifts of real estate, but they’d rather have the cash 51.

You can deal with fairness and empathy without being too charitable, that's not predatory dealing.I consider some methods of prospecting a bit objectionable, but what is your intent in following death announcements or medical judgments? 

What he ends up paying the management company may be far less than what he would pay in taxes for selling the properties.If he's charitably inclined there are a myriad of gifting strategies that can be used to reduce the tax burden as well as provide a stream of income.

If you feel charitable you can give the two girls 25 dollar gift cards.  

And thank you as well for your charitable work.. !!

Property 1 - Sell the property (you could 1031 it to better performing properties, or DST, UPREIT, or pay the taxes, (maybe offset some taxes with charitable gifting, or other deductions depending on your tax situation)Property 2 - Cash-Out Refinance - Pull out as much as you can, do the repairs and increase rentsProperty 3 - Pay off the property with Refi money, do the repairs and increase the rents.You would keep the two better performing properties, improve cash flow and investment returns.If you want to keep property 1,  I would refinance it and pull out enough cash to pay off the other two properties and do the upgrades.