The third person is a single female doctor.

Black Diamond is hosting the former Mayor of Worcester Tim Murray, who is currently the Executive Director of the Worcester Chamber of Commerce. 

Here's an article that talks about a court case that appears to address your question: https://fairhousing.foxrothschild.com/2012/03/articles/fha-basics/are-rental-roommates-covered-under-the-fha/(In the case, the court asked the question "If a tenant seeking a roommate expresses a preference in an advertisement for a female roommate or a roommate without children, does that person violate the Fair Housing Act (FHA)?" 

*While I used feminine pronouns as most bookkeepers (or clerks) are female, the best one I ever worked with was male.

I didn't want to spend a ton of money on my living expenses each month, but also didn't want to live in a sketchy area as a single female.

I was incredibly uncomfortable with the entire situation as I'm a 5'2, 120 pound female and when she was chatting with me, it seems like she wasn't in a right frame of mind.What should we do?

We did have the opportunity to meet the director of real estate for the City of Buffalo in person in January and she told us that we would need to show proof of the purchase price of a house and all the entire renovation budget up front in order to buy property directly from the city.

The opportunity recently came across my desk, and I’m really considering it but have no prior experience to go with.The Board of Directors has a proven track record with a previous bank that was acquired and from what I can see they’re all fairly heavily invested in the new venture as well (skin in game).Does this cause or raise any IRS/tax related issues that I should be aware of?

Looking for your thoughts and ideas  Without a direct or immediate need for the capital, I'd leave the equity alone. 

Loud music, slob, always using the kitchen/shower, says offensive things, etc.What if an existing female tenant isn't comfortable with the new male tenant you just chose?