It overrides the 1231 treatment you are arriving at. 

Also my electronic payers get the money to much much faster than the check payments which all seem to be dated for the 1st of the month but never arrive to me until the 8th of the month.

I have some money with Arrived and Ground floor, but not much.

Unfortunately after the housing crash, lenders stopped doing those. 

The government of Florida (and other states) require building inspections and money be set aside (Reserve Funds) to fix problems so that things like balconies crashing to the ground doesn't happen.Her HOA has underfunded their reserves.

Is it a gamble to move into one of these neighborhoods if the market crashes?

I recommend arriving at least 10 minutes early (depending on the event/venue) and bring business cards if you have them.

It's a feeling.And I'm surprised that you think the RE market can't crash 50% when it crashed 50%  between 2007-2012.

Arrive early and stay late.

You could, or the agent could explain how you arrived at the offer.