By putting the captial gains in a foundation and donating 5% to a charity, we would eliminate the pass through income gains.

Kind of like donating to a charity. 

When self managing, you've got to remember its a business and not a charity.   

My long term goals include financial freedom, time freedom, and the ability to help my family and then contribute to a charity or start my own. 

The coach is not a charity, but the coached do get rich.To sponsor, some sort of coaching is needed.

Like the gentleman above me said, you're not running a charity.

I'll try to keep this somewhat vague for the tenants privacy.I have a tenant who is provided longterm full housing support through a charity affiliated with HUD, they send me a check for her rent every month like clockwork.

If your intent is to operate a charity, please contact me and I will provide you with a list of very deserving organizations that will make better use of that money than your tenant does.If a rental is below market, the best thing to do is to notify the tenant and either raise them or get them out so you can place a tenant that can afford the property.

Sure maybe someone else gets to retire early or send their kids to college off your extra work but you could just write them a charity check instead. 

A charitable remainder trust is fine if he has a particular affection to a charity.