I would spend money to enhance and update to current standards the search functionality and person to person tagging so it's easier to find stuff.

That will be the best spot to meet an investor friendly agent in person or at least meet other investors in your markets that can help connect you to the right agents.

Quote from @Jeff Sanders: Personally coming from an agent/investor in CA, I always get a quote from a broker of mine and make sure I am knowledgeable with the fees/costs.

So it's just personal preference and budget for a host.

Apparently, the person I am under contract with was managing the estate of the actual owner who recently died.  

I take a picture of their driver's license.I ask for phone numbers that accept texts and any alternate land or business phone numbers.I ask for the names and birth dates of anyone under 18, and ask if there are any service / emotional support animals, together with their names and breeds.I also ask for personal references, previous landlord contact info (and length of time there), employer contact info (and how long there, together with earnings), as well as the name and contact information for their manager / boss.

You might want to explore DSCR loans, which allow you to qualify based on the property’s cash flow rather than personal income.

I personally think being a landlord in Chicago is easy and I have never had an eviction. 

Unlike long-term rentals, STRs can be treated as non-passive, allowing depreciation deductions, including bonus depreciation (40% in 2025) on eligible assets.For tiny homes, tax classification matters:If mobile, it is considered personal property, allowing 100% depreciation under §179, subject to income limits.

Questions they will have is who is the owner, what experience do they have, is their key person insurance against them etc.