The old saying is true, an ounce of maintenance saves a pound of cure.

I think you're being pennywise and pound foolish.

Tell the City to go pound sand because you don't own the property anymore.  

You can use Bandit signs, drive for dollars, pound craigslist for potential sellars.

For a flip, tile or marble surrounds seem really popular nowadays.Is this the 4-plex with the 600 pound shut-in?

Also if you ever replace your roof all the pounding will cause those.The garage cracks I wouldn't be too worried about unless they are opening.  

That would require us to empty out a unit with a perfectly good tenant, move into an apartment that we don’t want to live in long term, wait until our desired unit is available, kick the undesired tenants out after a year, and move for a second time...

There has to be a way to draft language that makes it undesirable for the tenant to want to sublease a space.

I've tried to sell these lots for $1000 over the past year and been told due to their location/slope, they are undesirable/worthless.

Redwood City has parts that are undesirable.