Yes, the landlord will have to pay the legal fees deductible on its own liability insurance, and will also suffer incredibly intrusive inquiries into every aspect of its business and personal life as the parties engage in "discovery" during the lawsuit.A third party who trips over a tenant's child's bicycle on the front sidewalk, and suffers injury and medical expenses, will look for somebody to sue.

Again, you can't be afraid of some trash on the sidewalks or unkempt lawns, but this area's property values have nowhere to go but up.

Some of the streets are less desirable because of the slope of the road/sidewalk and all the locals know you can't walk or drive on that street in the winter....something you don't know as a out of town investor.  

Things can look very different when you're standing on the sidewalk.

The new sidewalks and infrastructure have cleaned up the area and there are now loads of pedestrians and bikers that we didnt have before.

That's one month out of four gone.The Cape starts to roll up the sidewalks after Labor Day, but September is a great time to be there. 

Also sidewalk, curb and gutter may be required if it's not in place already.

I always have at least a $15k budget on our properties, there may be old asbestos siding in good shape but if it's ugly then we're going to paint it, if the porches on the front of the house are ugly, we're changing them, wrap the window trim in metal, throw a new roof on even if the current one isn't yet leaking, parge the foundation, replace the old cabinets, don't use $2/sqft laminate flooring, replace the dang trim if it's been painted over 100 times, remove the ugly wires from the outside of the house and have the cable company install new ones, fix the grading of the yard, trim trees, and repair sidewalks.

But if you've got huge 100+ yr old overgrown trees hitting the house or tearing up sidewalks, driveways, sewer lines & garages this is reasonable. 

Not only does it feel good, but I also notice things from the sidewalk I might miss while driving a car.