I got a feeling that life as a Private-$ Investor may be a great place to start, and these properties lend a perfect means to testing that out, solving 2 issues in 1 action, because you can JV your way out of the operational side of things AND retain that long term financial upside. 

We have an operational general contracting business here in Chicago, but we are slowly building technology solutions around it.Always looking to connect and talk shop around tech and real estate...would love to connect!

Do you plan to manage it yourself or look for an operator?

Most also rely on  beefed up rents and unrealistic operated expenses in their pro-formas to justify higher sale figures which appears to be the case here.

I self manage my own rentals and I also operate a management company assisting other investors nearby. 

I expect to be at least $40k (for 2 units that have been in operation since 1999 so well established) below my 2019 numbers (so below numbers from before any COVID impacts).   

It's a 2/1 with balcony and we'll operate it as a STR.

Well, several months ago I joined a brokerage and naturally I want to comply with their ways of operating and generating business.

This is typically raised from investors and it's used to close on deals and to operate the asset(s) after closing. 

Negotiation Skills: Whether it’s negotiating leases, handling vendor contracts, or resolving disputes, strong negotiation skills can make a significant difference in operational efficiency and cost savings.In my experience, a property manager who excels in these areas not only helps protect your investment but also maximizes its profitability.