You have debits of:$80K to seller$4K points$2K other closing costs$13K rehab into escrowFor a total of $99K of debits. 

Specifically this clause from the Fannie Mae website https://www.fanniemae.com/content/guide/selling/b2...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).

In addition, you lose the corporate protection if you improperly manage the funds, which becomes harder to separate if you have multiple properties unless you get multiple bank accounts, which also probably means multiple credits or debit cards for repairs, etc, or a separate management company with an agreement.I'm certainly not saying that there is no legal protection to multiple LLCs but I think you need to ask what is the cost to you protect yourself from the boogie man?  

That will cover paying off the hard money, closing costs on the new loan, and your pre-paids.

Automatic payments debited from their account won't matter if there's no money in there to debit.An extra half month's rent won't be much use if they're 1 - 2 months behind and you have to start an eviction.

Take the remaining amount and use 5-7k to replace the roof, ~10k to pay closing costs, legal fees, pre-paid expenses - unless it can be rolled into the loan - (and assuming we can get a conventional loan, otherwise, this amount may be higher for private money).

And if so, what would you ask for as additional security (much higher deposit, pre-paid rent, bank statements showing reserves, income tax returns, etc.....)?

Terms:30 year 4.875%20% LTV for a SFR25% LTV for a Multifamily$60,000 Loan (could be more but this is what we asked for)Closing costs about 6%Property taxes must be prepaid (as part of the monthly payment) for the first yearThis is a loan he applied for in his name only.

If you are paying for college you are already in massive debit anyway a few hundred more won't hurt.

Especially when meeting contract deadlines, HMLs ask for applications, appraisals, inspections, credit checks, upfront points, prepaid interest, etc. that can cause one to loose a deal.