I'm meeting with a couple agents i was referred to through my network and am wondering what critical questions I should be asking them to understand if they are the right partners for me in this market, especially considering I will be managing this investment from the other side of the country, and what info I should be prepared to provide to them.

@Matt Smith - as @Christopher S. mentioned you cannot use an ADU unit in Chicago as an AirBNB as the city's intent with the program is to provide additional affordable housing. 

I provided a free rent back for 2 weeks so the seller could get her funds and relocate.

You may want to make an introduction between your CPA to those 2 colleagues.The CPA can go over their services and pricing to your colleagues.I partner with many people on real estate deals - It never gets to a discussion on whether they do their own tax return or hire a professional.If a partner mentions he will provide capital - does he provide the capital on a timely manner.If a partner mentions he will find deals - does he find many deals and provide an analysisIf a partner mentions he will manage a property - does he manage the property well(find tenants, collect rent, communicate with contractors, etc)

We don't tend to get them when buying from a bank (because they usually won't budge on price) or wholesaler (who often provide an inspection) but do our own thorough inspection. 

Yes, it is possible to put lipstick on a pig, but in my 15+ years of experience providing property management, the best way to make the asset profitable over the long run is to do the repairs the right way from the start.

Quote from @Malcolm Brown: My real estate agent provides listings (multi family homes).

Found T&H realty services to be pretty interesting as they provide both buyer brokerage service (to help me find deals) as well as do property management i.e. they are not full turnkey provider necessarily, but reduces some of the hassle for me I guess as an out of state investor. 

what insurance protection does avantstay provide?

Property Radar does not provide daily data for FL which is where you are interested in doing your marketing or am i mistaken?