If you must walk on the driveway or sidewalk be cautious."  

It's across the sidewalk leading to a gate to get to his vehicle.

In a KFC lease, tenant most likely is responsible for sidewalks and parking lots, etc. in a multifamily, you are likely liable for anything that happens in the common areas. 

If the claim was for say tripping on a damaged sidewalk, Tom is probably not personally liable, but maybe you can get the management company and maybe the LLC itself. 

This property is next to the historic downtown area so there is plenty of foot traffic on the sidewalk for a small business, but the garage is located on the back of the property.

Investments are being made on Main Street with new roads / sidewalk / tree planting improvements etc.

Then I add a buffer in to cover siding, sidewalks, etc.... usually comes to about $70/month if I've replaced those items during rehab, but more if I have left existing in place

The non-cosmetic issues I'm dealing with are: a driveway and sidewalk sloping towards the house, a foundation issue, replacing the water lines inside the house, and removing a wall between the kitchen and living room to make the space seem bigger.Other than that I'm putting in new trim and doors, finishing hardwood floors, redoing the ceilings, painting the cabinets, etc...

Community pool, clubhouse, gym, sidewalks, playgrounds, security cameras, and pavilions in place.

Our plow guy will be there very early, around 3-6 a.m and will move all of the heavy snow out of the way, as well as snow blowing sidewalks.