If you can't keep control of your personal finances, you are highly unlikely to succeed in real estate investing.

I wanted to start by house hacking but (1) I am not allowed due to strict HOA rules and (2) my city isn't as desired as the next city over.

You have to get the person face to face.Creative deals are negotiated. 

It all depends, this is why I always review potential client's books what is the best course of action.I personally do not like QBO for real estate (I make it clear in all my posts lol) I just renewed my certification just because most people can't afford the PM software with accounting such as AppFolio and Yardi.

Quote from @Russell Brazil: In the future, do a court records search at https://casesearch.courts.state.md.us/casesearch/If you had done that, you would have seen they have 8 failure to pay rent cases against them.I am curious Who did the initial check on this person?

If you get a bad tenant, the rest of your tenants have to live with this person until you can successfully evict them.

Is there a specific name for this person or could it be anyone in the bank? 

I will note, personally, I am a passive investor, as well.I would generally agree with your assessment.  

Highly desirable as a rental with the potential to convert the vacant lot to additional STR units.

@Matthew RolfI’m not doing a crash pad I’m house hacking a 5 bedroom house which I will live in here in a few weeks and rent the bedrooms on 1 year leases to pilots and flight attendants I’m personally friends with.