This is a Chicago landlord problem, regardless of if the ordinance affects your specific area.

I am looking to focus my investing on the commercial space specifically value add apartment complexes.

I learned a lot about managing an STR, specifically with revenue management and guest messaging.

What about something like this: https://www.realtor.com/realestateandhomes-detail/1328-Ridge...?

Any specific contract clauses or safeguards I should include?

I’m concerned mine is not detailed enough.  

I know the potential state specific trigger if I transfer to my LLC in future, but difficult to obtain loans in an unproven LLC's name. that being said, do I insure the address under my name or the LLC listed on the STR business license?

If the goal is to become a full-time flipper/contractor, then doing tighter jobs can help build momentum for a business, that will pay dividends well beyond just the specific house, itself.  

Is the description detailed and appealing?

Lenders typically require at least 15-20% down for multifamily properties, depending on the specifics of the deal.