My thoughts are to remove the shingles, tar paper, replace any rotten wood areas, then cover it up. 

To learn more about this, see the following: https://www.irs.gov/retirement-plans/2017-ira-deduction-limits-effect-of-modified-agi-on-deduction-if-you-are-covered-by-a-retirement-plan-at-work

You could simply get a personal loan or 401k loan (if possible) to cover the renovation.

RelocationsAccording to HUD 4000.1, “A Borrower may be eligible to obtain another FHA-insured Mortgage without being required to sell an existing Property covered by an FHA-insured Mortgage if the Borrower is...relocating or has relocated for an employment-related reason; and establishing or has established a new Principal Residence in an area more than 100 miles from the Borrower’s current Principal Residence.

Insurance may cover certain indemnity obligations, but not always.

Its important to know when they will need replacing and if you'll have built up a large enough CapEx reserve to cover the cost or if it will eat into your cash flow.

The company I'm buying from agreed to a higher price at the first closing to cover the taxes and subsequently closed.

If your IRA is short of funds for the downpayment, your SDIRA may partner with other self directed IRA's to obtain the necessary funds for the downpayment, closing costs, and reserves necessary to be available to cover operating expenses.Any further questions, you may PM me.

The standard 10% usually covers tenant management only - advertising, screening tenants, preparing leases and renewals, fielding phone calls from tenants, collecting rent and conducting evictions.  

I have seen 4 units come available in DC where the rents would cover or almost cover the entire mortgage.