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.

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.

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).

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

If the water heater is leaking one cup a minute and going down the drain, they can shut it off or monitor it until Monday.

We did the following inspections:1.) drone inspection of the roof. 

That's one of the main reasons these houses get abandoned, that and bad roofs but you can probably tell that from the outside.