As for rents, they should rent out pretty easily in this market since most of the rents are 900-1200. 

You said it isn't obvious that it's coming from the roof, but if rainwater is coming in from one damaged area it can easily be pooling and then traveling to that area of the house.

Remember with every rental purchased you are planting seeds for a tree that will mature to provide fruit forever.

I always have tenants provide me with an emergency contact.

First, as Tanner suggested, engage a general contractor to assess the property and provide a detailed rehab estimate.

Please note, based on the numbers provided you will not be cash flowing. 154k loan amount - 30Y fixed  4k in annual taxes & Insurance 7.75% Rate Monthly PITI Payment = $1,436.60Your estimated rental income is only 1k-1.4k per month.

Emails and voicemails are do not always provide that assurance.

@Drew Sygit I noticed you provide property management services. 

You'll need to provide Entity Docs for each LLC that is a part of the transaction so that the underwriters can review them all the way down to the natural individuals/warm bodies. 

Surveyors are always provided by the owner.