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.  

Could I go out and really pound the agent business and be a high income earner?

I’m no person able to give legal advise but based on what you said I’d tell the guy to pound salt !

The 800 pound gorillas (in no certain order)  in this space are  Property Ware,   Appfolio,  Buildium  There are other options depending on the number of properties you are managing and what you expect your growth trajectory to be.  

If you want to wait and see what happens down the road you can always tell him to go pound sand.