I am based out of Chicago, il

It may also be difficult based on the figures you provided. 

The real obstacle is not the STR loophole itself but the tax benefit that it's based on.

What kind of database should I use to keep track of my leads and client base?

It really becomes a time value of money calculation based on when you want to sell your Class A rental.

In almost all investments, you should have a solid base of reliable, cash-flowing, and hopefully appreciating assets before striking out into something new or riskier. 

Just keep in mind that there are further steps you'll want to keep to minimize the possibility that your entity is ignored for this kind of personal liability (say, if you were the person who didn't properly clear snow, or if your finances and the LLC's are comingled).And I agree with @Chris Seveney, insurance may provide adequate protection based on what's available to you.

Shared housing provides affordable, flexible rental options for young professionals, remote workers, and students.As shown above, co-living properties have more demand than traditional two-bedroom units and appeal to a wider tenant base.2.

Is the paint latex, oil or water based?

I don't get the term "DSCR loan"   I mean all loans for 5+ units are based more on the property than the buyer.