Keep in mind you need a capex reserve!

You'll pay more in fees, but you can keep your cash available for reserves or your next deal.

To say the least he is not able to do a full rehab himself and all of his reserves go to medical bills.

They generally want the same information, 2 year's tax returns and W2's, 1 month of paystubs, 2 months of bank statements and 6 months reserves.   

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Another thought would be a lease with exclusive option to purchase: you pay rent for X-months and give the Seller a fee to reserve the property for you to purchase sometime in the future at a price you agree on today, and at the end of the lease you hopefully have your job and can buy the property using traditional financing.Good luck!

Also having strong cash reserves can ease the burden of negative cash flow certain months if you are trying to ride some appreciation.

Old systems breaking can eat into reserves very quickly. 

I'm waiting to hear back from the County Zoning Department to gather more info on potential uses and confirm that it is SFH ready but in the meantime, I'm wondering if anyone has advice on the following: 1) Should I be concerned about the existing trailer and barn (and possible need to remove those?) 

The floor is the starting rate of 4.2 i believe it was, and as far as Caps, again i have to confirm that.