@Greg StrunakA good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

I would recommend shadowing a few loan brokers for the first 3 months being newly licensed. 

STR management is 20-25% (I would recommend self managing or getting a VA), since income is higher you could probably get away with 5% for maintenance / cap ex but remember you need to cover utilities and cleaning for these units which drives up costs.

I highly recommend an ACH service.

Buyer's agency agreements were already required here before, our regulatory agency just went from strongly recommending them be signed right away but not really requiring them until writing a contract to 100% requiring them to be signed prior to showings.

I recommend having an attorney draft one that can be short.

If it is unclear as to whether you have met the standards of the Illinois Code, it is recommended you speak with an attorney for an explanation of Landlord/Tenant Law.

How would people recommend approaching the initial set up of that property with an eventual exit (via sale or hand-off to PM/operator) in mind? 

I also liked that they are US based as I had issues with my bank with the Finland based Hostaway.Finally, I highly recommend PriceLabs.

Can anyone recommend software which would accept monthly payments (from me to seller) and create proper 1099 forms for tax purposes at year end?