The best thing you can do is to get in touch with a few lenders and walk through your specific scenario. 

An additional benefit of a detailed engineering-based Cost Segregation Study is that it can increase potential insurance premium savings as well as provide support for the property tax appeals process.

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

I am looking to do some updates and touch ups in basement unit as well.While the house zoning requirements comply with ADU requirements, the basement is not up to ADU standards (ceiling is too low and one entry). 

With no credit score the interest rate would be based on the lowest credit bucket.

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

I am based out of Chicago, il

You are in a great place to learn based on the successes and failures that many have had.  

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

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.