The overall impression I got from others was that it would be better to either establish a non-profit or to go the traditional route and pair it with charitable donations on the side.  

I see myself giving back to the community via donations, starting a foundation, and possibly opening up a homeless shelter in my hometown.

If you haven't yet donate $100 each year to their office and it will go along way. 

Used furniture or donated clothing are common sources.

Maybe I will Craigslist free item them or donate to Habitat for Humanity.

Maybe donate all the earnings to a charity, but then you would not be paying taxes because you have no earnings.Only sure way to not pay any taxes is to give up US citizenship, but that is perhaps beneficial only for older retired people.

With the boost to my tax returns (now amplified by home ownership; I donate a lot to charity so I always get a return anyway) and expected appreciation, it may all even out or better.  

I simply told them if they didn't need the assistance I would like them to donate the money to someone who does, but obviously that is up to them.Now if I had someone who moved in a few months before I would be far more cautious about what they are requesting.  

The house is filled with junk from the former owner and tenants and I'm learning all about which donation/recycling center take which materials.

You can donate to your favorite charity for the tax deductions.