It sounds like the Title Co. was not aware that the tenant prepaid rent and just prorated the current rent for the month of closing, so agree if they had no knowledge of it, would not have ever gone on the settlement statement as a credit to the buyer and they likely will not do anything post closing to help obtain those funds. 

This will vary based on region but in general 2 – 5 points, 9% - 16% APR (meaning this is the annual rate so divide it by 12 to get the monthly interest amount), and documents fees can be from $600 – $1,900.

I'm hoping they'll just go at the end of the month.

This is usually a 12 month commitment that is "Interest Only" and after you finish the rehab and get a tenant, then you refinance into a DSCR loan.

Have we tried asking him if he is interested in steady monthly income backed by real estate?

The 6 months was up on 1/1/2021. 

If you are setting aside funds for capex, taxes, insurance, or other expenses that don't occur monthly, transfer those funds to Savings each month and hold them there until it's time to spend them.

They have had 100% occupancy at market rates and currently bring in around $2,000 per month in cash flow.

House hacking seems like the best strategy for me.My goal is to purchase a single-family home in Maryland, D.C, (from lurking I've heard D.C was terrible for investing) or Virginia with multiple rooms where I'm making monthly payments similar to what I pay in rent and other charges ($2000-$2500).

No deal(s) just insights & offers to obtain a premium membership that cost ten times the membership you already have (with monthly or annual dues).