Anything beyond that is charity work and should be handled by your institution of choice.Good Luck and Good Investing

My ultimate goal by the time I hit 45 years old is to give $5000/monthly in charity. 

Does anyone know of any organizations/charities that offer rental assistance in Montgomery County, Maryland?

It's not fair to me to not know for sure even if or when she will move or when I can have another tenant move in.Its fine to be nice but this isn't a charity I am running. 

Some people give to charities, you like to give to banks.

So you give $100k away to a charity and you have a $50k cost basis on the remaining property.

It's a strict 2-year requirement.As for strategies to avoid capital gains on the sale, if your client doesn't meet the ownership and use requirements for the Section 121 exclusion, they might explore other options such as:1031 Exchange: If the property is an investment property rather than a primary residence, your client could consider a 1031 exchange to defer capital gains tax by reinvesting the proceeds into another investment property.Installment Sale: If your client is willing to accept payments over time, they could consider structuring the sale as an installment sale, spreading the recognition of the gain over multiple tax years.Charitable Remainder Trust: If your client is charitably inclined, they could contribute the property to a charitable remainder trust, receive income from the trust for a certain period, and then have the remaining trust assets pass to charity upon their death, potentially reducing or eliminating capital gains tax.These are just a few options, and your client's specific financial situation and goals would need to be considered in determining the best approach.

@Nathan Gesner 1) if you’re investing with a spouse make sure both are on board for self management or it will harm the relationship. 2) it’s a business, not a charity, so if you’re susceptible to hard luck stories from applicants/tenants, don’t self manage. 3) water heaters, heat and a/c, plumbing only seems to break down when you’re finally on vacation, so have good contractors in place who will go on your call and let you pay them from out of town.

The car company and the cell phone company understand that they are not running a charity. 

Only other way is donate all the gains to charity.