Of course whether the property is neat and orderly, has a floor plan that is functional and a style that is easily compared to other properties in the neighborhood matters as well. 

@Michael Biggs I love your style.

My PM tells me we may need to dig a few feet down to try and repair the leak after the next rain and we've been able to positively ID the general leak location.My question is, other than interviewing folks during DD, what is the best way to determine issues that are only present during certain environmental conditions (i.e. high winds or strong rain)?

A lot will depend on your personality style.

Legacy-style holdings are for your own capital. 

But in older areas with a lot of different styles it might not be so easy, so the agent would need to make adjustments.With the RPR analysis in hand, you can make your ARV assumptions based on the work needed.

Financing can be "easier" since lenders will take into account the existing rents but do make sure to research thoroughly and have experienced mortgage / real estate / legal people on board since the commercial realm, even at an entry level, is a whole different level of complexity and risk (zoning / permits / environmental / leases). 

SDIRAs for real estate are not for the "fly by the seat of pants" style person.

Then they sit with all these houses that are slowly but surely losing that new home/latest style appeal and try with the incentives again.I doubt anything will change this time around.

It's much less visually confusing and straight to the point.THe header of my comps looks like this: Style Rooms Beds Baths Sq.