There are risks of course, largest one being that if you lose your job, the funds are due back within 60 days or it's a taxable event. 

@Minh Le Yes, your seller can sell to someone else, you didn’t close by the closing date and he has no obligation to extend it.As for the EM, if you are in default, as per your contract, and you refuse to sign the em release, he can either force arbitration or sue you, as per the contract, you’ll lose and pay his attorney fees/costs on top.  

A commercial broker in your area would really help guide you on your first deal.Roughly it looks like this property has a big risk of losing all tenants.

If I consider cap ex and repair reserves, I'm pretty much breaking even every month (and arguably losing a little depending on how much one thinks should be budgeted for repairs/vacancy). 

On a conventional loan (at least 5% down) you can possibly lose the PMI by getting an appraisal when you have 20% equity.

Con lose $14,000 of value before calculating the costs of sale. 6% commission is another $7,560 Pro rata taxes at sale say $2,000 to $3,000.

No one can get anything done because they look at my farming income and say I am losing my butt.

Talk to a CPA.I think if you go too far into the weeds with a cash out refi and sub2 you will lose them for sure. 

Hey Morris - in South Carolina where I invest, a tax deed "wipes out" the mortgage and that lender loses their money because the property taxes are in superior position to the mortgage.

I would hate to lose this deal over 2k but feel like he is being shady with his agreements and its sending up a lot of red flags my way.