➡️ Has any work been completed on the roofs in the past ten years?

Is there a valley in the roof above that area- looks like no gutters and a valley in the roof causing water to erode?

I.e. roofs cost $6k+ for me, HVAC going out can cost $8k+.Tenant Risk: this is the most realistic one, in my experience.  

Completed high value renovations to boost market value - new roof, etc., What was the outcome?

@Ben BolingbrokeI would tend to spend my 30k on a new TPO roof or marketing to find deals, however, I think if you can get going on MF investing then 30k is an insignificant rounding error.

My employees wash their vehicles and muddy equipment every day and they put a massive amount of rocks, nuts and bolts, wood and all sorts of debris into the pump and it never failed one time.Since my pump handles both rain water and the water my employees use to wash their equipment every day I installed a specially made system with electronic valves that makes the water they wash their equipment go into a sediment and filter box and then into the city sewer system and when it rains the electronic valves have a sensor that detects water coming from the roof drain downspouts and valves switch to make the water from the parking lot go into the street.

Just get yourself in the game and own the roof over your head with a monthly mortgage you can afford comfortably, anything beyond that rent the other rooms out if there are any.

We need to repair a small portion of the roof in detached garage in multi-unit, in Evanston.

Similar to the way a new roof helps an exterior.If you look at professional product photos for homewares, there is usually a single (or at most a small handful of) non-neutral color(s) that is repeated throughout various elements in the room (area rug, throw pillow, bed scarf, vase/sculpture, picture etc).

Every mod I have seen uses truss system roof framing.