Lets say you own a store and somebody slips and falls on your sidewalk. 

I am looking at a few homes I expect to go in the 200-250 range (just guessing based on knowing area values and what I can see from the sidewalk at the houses).

All states are a bit different, but most require certain requirements regarding shoveling/snow removal on sidewalks, parking lots, etc; especially parameters around removal after snow fall has stopped.You want to ensure that whatever he's doing is adequate to protect you against someone slipping & falling on your property and trying to assert a claim.

If you're in the North, wait 3 days after a snowstorm and make a list of all homes where the parking or sidewalks haven't been cleared. 

Maybe infill lots with existing roads, sidewalks, drainage, utilities, etc. in the best of area would be that high.  

It's the same false argument that people make (or used to make when he was worth considerably more money) about Bill Gates being so rich that if he saw $1,000 on the sidewalk in front of him it would not be worth his time to pick it up because he makes $300 a second and it would take 4 seconds for him to pick up the money.  

The new inspection states that i have trip hazards on my sidewalk and the regrading needs to be done around the home as well.

Think about the dirt they pick up after walking around the block, stepping in water, dirt, mud, poo, and the general filth on the sidewalks/street.

"I noticed today that there was a piece of gum on the sidewalk in front of your property. 

Use a sidewalk scraper to pop off the pad staples and carpet tack strips in a flash.