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

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?

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.

The best coverage is generally called "Special Form".  

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.

It is a little tricky and risky, but possible, you would need to make arrangements before the auction with the auctioneer and permission of the trustee to have  immediate possession of the property. 

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. 

I specialize in home remodeling.