Here's how I do my due diligence:1) Portfolio matching: (takes 30 seconds per deal)a) Have an educated opinion on where I think we are in the real estate cycles (financial and physical market cycles)b) Then and only then do I pick the strategies, capital stack, and specialized asset subclasses that make sense for that opinion.

But they really have their niche down are creating a special experience for guests and not simply selling accommodation.

Thus, adding any amount of interest on a second is irrelevant if you lose everything.We know a few who specialize in seconds and consistently lend behind us.

For those landlords who take security deposits in City of Chicago, is a separate business bank account sufficient for the security deposit or do I still need to set up the special landlord account that requires all W-9 paperwork from tenants etc?

The best coverage is generally called "Special Form".  

If the lease sets forth how to clean these units with a special cleaner it seems charging the renter for the damage would be a possible move.

Or is this just a theoretical way to gift an asset, but on paper it remains in the parent (grandparent/ gifter's) name?   

I’m sure they exist somewhere, but the vast majority of small businesses just don’t generate the income nor the margins to hire the quality of people nor the specialized skills needed to produce without the involvement of the owner willing to wear many different hats, pick up the slack where needed, and work the hours necessary to make the business a success. 

Would really appreciate any insight you have on resources I should look into to learn more, point me to companies that specialize in this, or anything you think I would need to know to get started.

You will certainly come across several groups in the Austin area...but none will only specialize in Section 8.