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.

We often use the Charitable Remainder Trust (CRT) as a starting point if you have no control over the type of income.CRTs not only let you take charitable deduction up to 60% of AGI, but you also can create a stream of income from the trust for yourself. 

Account Closed  You can take the standard deduction, or calculate your itemized deductions on Schedule A - things like interest you paid on mortgage for your primary home (that you live in), property taxes also paid on your primary home, charitable contributions, medical expenses (over a certain amount), etc .  

For a more straightforward way of distributing it tax-efficiently, you could give it to a charitable entity, so if they are part of one that would be easy-peasy.

It's hard to give/receive advice without more specifics, and you didn't buy the home to be charitable.

If someone choses to allow their business to be charitable good for them but for most of this this is not feasible .