They should own, renovate, and manage the property all under one roof.

Up/down double $57,000 purchase price (hopefully less)PITI = approx $500/mo with 25% down conventional loan$14,250 down + closing costscurrent rents total just over $1200/mo for both - leases in placelandlord currently pays about $200/mo for water/sewer/trashI figure about 10% vacancy and 10% maintenance which leaves me with about $400 monthly cash flowThe two major concerns I have are that it needs a new roof (tear-off) and that it has a funky layout.

The roof was re-done prior to me buying the place which I knew but being young and naive and didn't realize what else needed to be replaced. 

Up/down double $57,000 purchase price (hopefully less)PITI = approx $500/mo with 25% down conventional loan$14,250 down + closing costscurrent rents total just over $1200/mo for both - leases in placelandlord currently pays about $200/mo for water/sewer/trashI figure about 10% vacancy and 10% maintenance which leaves me with about $400 monthly cash flowThe two major concerns I have are that it needs a new roof (tear-off) and that it has a funky layout.

Roofs, vehicles, furnace, etc are each depreciated on their own schedule as defined by the IRS.

I'm trying to understand what you can put as a contingency since there no roof or foundation to blame and get out of the contract.

I always check the foundation, roof, hvac, sewer (septic), windows.

My own roof has lathe installed because it is my preference.

Roof 15 years old. 

Tenants do not have the financial wearwithall to handle roofs, ACs, furnases etc etc.