I look at it from a life safety point of view. If the lack of repairs make the property unsafe, then do the repairs. Life and limb outweigh the owner's budget and profit. Examples would include sidewalk and/or parking lot trip hazard repairs. How much alligatoring is too much? Would a reasonable walking client trip? Some areas have definite metrics about cracks - we use 1/4 inch difference in elevation.
I also look at it from the legal standpoint - if the law requires the repairs, then you have to do them. For example, elevators in our state must be inspected annually and conform to a checklist provided by the State Division of Building Safety. Every five years the state sends an inspector. The property must fix anything that does not comply within 30 days after the inspection. I know of one instance where those repairs cost more than $25k - whew!