I am also a realtor that handles 15 properties and different companies.

But, unfortunately, most people ordering appraisals these days (typically AMCs - appraisal management companies) don't pay enough for good appraisers to accept their assignments, and therefore, many appraisal reports lack good results.

Check the reviews for companies you’re considering.  

That means a column on a spreadsheet for each property (tax number) and a comprehensive list of items on the row side of the spreadsheet.I want to look at what my exit strategy is for each building.I want to know why he is offering seller financing and of course if it's a fair price, has title reports and is done through escrow.I don't need a real estate agent, but I would have inspections done to look for something I night miss.I want to know if buying the lot and selling off a portion makes sense.

Is the management company financially secure?

He contacted my friend's company and they moved it along to me.

Any recommendations on an AirBnb Manager in Chicago to take over an existing asset?

Contacted sewer company with whom I have a contract /insurance again. 

As far as finding the right markets, the BP podcast called "On The Market" shares reports of best markets as do other platforms but BP is my fav for sure.

In future years’ budgets, the association should consider budgeting for an Operating Contingency (funds not earmarked for any specific expense) or should consider creating a line item specifically to fund Prior Year Equity in order to bring the balance into the 10-20% range.If the board doesn't know what it is doing financially then they need a management company that does along with an accountant that understands how HOA's work.