I prefer graduate students whenever possible because they don't have time for partying, are of legal age anyway, and generally tend to be by themselves or with a partner so it's more like renting to a couple.

.❌ Legal Risks – Chicago has strict landlord-tenant laws.

I think hard money lender to take this risk cannot legally charge appropriately which means the law is working against you (the law meant to protect owner occupied owners from unfair loans).I agree with @Jay Hinrichs that your best option likely is to sell on the mls.  

Certain neighborhoods do not allow STR so be sure to check the restrictions when looking.

Restricted food benefits, no fast food and cheetos, no, basic food, basic everything, SURVIVAL. 

These 2 platforms don't focus on MTR but vacation rentals so using Furnished Finder is a better way to get those longer term folks.I have always been a bit concerned about the area's penchant for restrictions.

I don't know if SF County has restricted the AirBnb licenses.Jens

Registration is only permitted for legal entities, partnerships and natural persons who are 18 years or older.

There are also 'mezz' lenders (typically for larger transactions) who will cover up to 90% CLTV and require you to bring the remaining equity to the deal, and additionally there is Gap Funding in the form of unsecured personal debt.The latter can potentially be the most expensive option, but allows for true 100% financing as there are no restrictions for how to use these funds, as they are unsecured, and generally obtained through personal credit, income etc (since there is no collateral for obtaining these funds).

An LLC is useful for two things: anonymity and legal protection.