The city isn't going to play hide & seek.

You should have stopped dead in your tracks as soon as the agent could not tell you why the seller could not be out by the 3rd. 

There are several different issues at play here. 

As long as you are abiding by the Fair Housing Act and not making a decision based on any protected class, I think you can ask anything you like (e.g. do you play chess at the grand master level?

Investing in real estate can most definitely produce a good positive cash flow for you to never work again, if you play your cards right.

I am trying to understand all the parties that can be involved and at what point in the timeline they play a role.

Probably busy out buying quality assets that help you meet your goals instead of playing amateur macro economist. 

At the start of the auction they may withdraw some of them.If you want to play this game you should have a number of properties in your pipeline. 

It's a long term play.

Many open houses are dead but things should pick up in September.