Off-market properties oftentimes have tenant, condition or title issues which may make it tough for you to get FHA financing.

Unless you have some money, skills, something of tangible value with a proven track record, it's going to be tough to get funding.

So,does it still really sound all that tough?

What little understanding I have of your part of the country is that it will be tough to find properties that actually cash flow.  

I'm having a tough time finding someone to take on a job of this scale since it's so small, and likely only a day of work.

The tough part of your question is that it really depends on the amount and type of work that needs to be done for your roof. 

@Robert M Ericksonnon owner helocs are tough to find after the mortgage markets crashed.

Lenders got tough with this about 20 years ago, and among the various documents borrowers sign at closing are affidavits attesting to the source of down payment.

., our agent is our co-worker.

As a general rule of thumb you'd want your house to be situated in or very near highly trafficy area to generate interest and for an easier access for your workers and family members of your tenants.