They're both great imho.Hoboken will be fine in the long run, but your intuition about a soft patch is most likely true.  

@Aaron PetersonI moved your thread to the landlords forum.Snow removal ... it will be here before you know it ... .I've already put our RFQ as we were not happy with our service in one city last winter.In our experience, when it comes to landscaping/lawncare and snow removal, anytime you cannot define where one tenant's domain ends and another begins, the obligation falls to the landlord.If you have a side-by-side duplex or a row of townhouses where each tenant has their own drive and patch of green, you can hand-off snow removal and lawn care to the tenant ... though you are just as often better served to take care of it yourself and bake it into the rent.Anytime you have stacked units or a block (such as a small purposely built quadruplex), the parking and green space are common areas (just like stairwells in the interior) and fall to the landlord.

I also patched it up with caulk and a lot of latex paint.

The key here is to know what's in your HOA documents.Generally what happens in a situation like this is that you would make a claim on your insurance and then they would subrogate it to the responsible party (either the HOA or the other unit owner), so I'm surprised that your insurance company is giving you the run around.Make sure you've got a written statement from YOUR plumber indicating where the plumbing fault came from and, before you patch the drywall, get the HOAs plumber in to look as well (if they have one).  

If all else fails and it gets damaged, it's possible to remove the damaged section and patch the floor carefully.Tile is a slightly different beast.

Horrible experience with patch of land so far. 

Say my tenant broke something that I could easily fix myself like patch a large hole in the drywall or replace a few broken tiles.

Nails will be patched up and you will have to paint all the spots. 

I once swapped out a vanity without realizing that the new vanity was slightly smaller than the one I took out, so the wall had to be patched around the entire thing.

One unit is in good condition while the other will need new flooring, holes patched and a full interior paint.