Scammers will ask for prepaid credit cards or for you to Venmo them money in advance for due diligence fees.

I DARN well hope that $1550 “escrow fee” is an example of someone bad at their new job and is really just prepaids  Hopefully someone from the Chicago area will weigh in and say you didn’t get as hosed as it looks  Ps  a lawyer fee?

That leaves about $225,000 after payoff of your current loan, and after the upfront costs and prepaid taxes/insurance associated with the transaction (ballpark of $10k), you could be looking at around $215,000 or so.

He said that he expects that I refund him the March rent that he prepaid since he is giving me more than 30 days notice. 

Good point @Stephanie P - "The new loan amount can be no more than the actual documented amount of the borrower's initial investment in purchasing the property plus the financing of closing costs, prepaid fees, and points on the new mortgage loan (subject to the maximum LTV, CLTV, and HCLTV ratios for the cash-out transaction based on the current appraised value)." 

For the vast majority 1 LLC and 1 checking (operating account for income and expenses) and 1 savings account (for security deposits and prepaid rent) and then as @Nathan G. says over here you might find a 3 account useful:  Do you have one bank account for all of your LLC?

In addition to closing costs, you'll also have 'pre-paids', which are the property taxes and insurance premiums you pay upfront at closing.

For example, If you're buying in August and the seller has paid their taxes for the full tax year (July 1-June 30) of the current year, your closing costs will include reimbursing the seller for 11 months of prepaid taxes.

We have taken prepaid rent in the past but never at a discount. 

At closing we prorated the paid rents and taxes, but they were prepaid, not billed later.