It fronts directly on the sidewalk in front of the house with one basement window visible from the street.

The responsibilities are written into the lease and I go over it with the tenants.With multi's especially on the city, tenants have a tenant mentality, and customarily they pay the rent, expect the sidewalks to be swept, garbage taken to the curb, grass if any mowed.

There is some cracking along where the house meets the side walk and driveway conrete (should form nice sealled 90 degree angle).

When it rains, it stays flooded in that area for at least 2 days near the sidewalk.

The sidewalks are all broken up- this will be fairly expensive to repair if I hire a professional.

For example, your contractors or a random guy walking on the sidewalk outside your house, where he slips and hurts himself...

But they are real estate professionals, many with formal research and investigation backgrounds and all with million-dollar pockets, and casual here-today-gone-tomorrow looky-lookies are not going to compete successfully with them.The best advice I've ever heard about spending money at the auction went something like this: if you can't afford to drop the money you've budgeted to spend at the auction in a pile on the sidewalk and burn it right there, if your business model can't survive that, don't bid.Again, I would say a real estate auction is a great place to learn a lot about real estate by studying and watching, but it's not a place to learn by trial-and-error.Best of luck to you.

There is a famous case in San Francisco a few years ago where a local couple bought the HOA property like sidewalks and streets, in an expensive neighborhood.   

@Caleb Heimsoth Single family with a short, one-car driveway and small amount of sidewalk.

Maintenance is on us in MF for the common areas (weeding, trimming, external lighting, hallway cleanliness, carpet cleaning, salting sidewalks, etc.), whereas in SFH I just let my tenants take care of all of that.