Just give them the details of the property, beds, bath, garage, exterior, age of roof, as much as you can, your asking price, whether seller or buyer pays closing, and the rest is on their end. 

This house needs a new septic system, foundation, siding, roof, and there are mice in the walls despite all the poison I've put out, etc. etc.  

I work as a roofing salesman and earn 200-300K per year.

Make sure you have cash flow, $200 a month is usually what is needed to break even over time (in my area), roofs, ac, and other big ticket items only need replaced every 15-20 years, but you need to build a cusion for it.

When was the last time maintenance roof/parking lot/ other was done to the building?

Roof; Furnace; Basement upkeep)?

It's impossible to tell from the photos what condition the home's mechanical systems are in or the condition of the roof.

I'm an experienced roofer and general contractor with my own company LLC Roofing and an upcoming real estate investor.

There is a hole in the roof that we could not see and the water damage was neglected for likely years.  

Here are some other things that could go wrong which may cause failures:Unknown necessary repairs (i.e. sewer lines, roof, etc)Not having cash reserves to cover vacancies / major repairsUptick of crime / vandalism in neighborhoodVandalism of propertyInfestations (pests, other)Bad tenants / No tenants / tenant family issue impacting stay (i.e. death, divorce)Rezoning of school districts / Loss of accreditation of school district Insufficient Property Management (not addressing tenants concerns, no notification of repairs timely - causing further damage, etc)Not following market pricing on rental / raising rent to frequently or too much at onceLegal issues (i.e. tenants sue for injuries on property, taxation, etc) I think you get the idea.