I also read the city's master plan and they are working towards converting a popular street into a more pedestrian friendly walkway with sidewalk stores and restaurants.

Stamped concrete drive and walkway.

Fresh mulch, pavers for the walk way, a japanese maple tree. clean cut lawn. some night lighting for the walkway 

Purchase price: $210,000 Cash invested: $10,000 Sale price: $285,000 Updates completed in this home all by my wife and I unless noted:New Roof - ContractorCedar Garage Doors - ContractorPainted Exterior Painted Interior and Design Walkway to PoolPlaster, Prime, Painted PoolBarn Doors and AccentsCedar StairwayWindow TreatmentsHand Built Cedar Fencing - ContractorTheater Room Wiring and Sound What made you interested in investing in this type of deal?

Condition of the propety (walkways, driveways, steps, porches) from a safety standpoint5.

What about fixing/updating the walkway leading up to the front door?  

Now, the plow doesn't come for anything below 3 inches, and I guess my question is - is it unreasonable for me to expect my housing tenants to shovel their walkway/around their car for under 3 inches of snow?

Too easy to create a hazard either from protruding into a walkway where someone will injure themselves on it, or it will be draining condensate onto the sidewalk that they do not clean, creating a slip/fall hazard.

Easier said than done though given you would probably have to go through a concrete slab to direct it away without interfering with any of the walkways. 

Just looking at the picture and seeing you have a walkway at the end of the wall, I'm guessing that the wall is not load bearing.