I also check to see how many other properties this same landlord owns, so I can have a casual conversation "landlord-to-landlord" being careful not to say anything discriminatory of course.

These were properties the sellers didn't necessarily want to actually have to finance, but since the houses lacked the maintenance and lacked the appeal to go into the MLS, they were told by the agents to take care of it so it could be listed.

It is more of an issue to be very prudent in your tenant selection process.  

I know you manage all your properties here in Chicago by yourself but do you know any reliable property management company in Chicago that can take care of my rental properties ?

If you are only flipping a handful of houses a year, you can probably get by with a spreadsheet, but here are some important items you need to track/consider for tax season & business management:Tracking Project Expenses & Revenues to calculate your project Net ProfitTracking Assets/LiabilitiesProfit & Loss Statements showing Profitability of each projectTracking how much you paid each vendor/contractor for filing Annual 1099sActual vs Budget Tracking so you can see what repairs were over/under budgetBank reconciliation to make sure your accounting books match your bank statementsProvides a history of the business, so you can track financial progress or pull past financials in case of an Audit

We didnt really care, that could be chalked up to difference of opinion.Heloc applied for to be taken out. 

On this, I advise that you be careful in your spending.

That takes care of monitor & computer all in one, and if space is really at a premium you can use the dining room or kitchen table as your office desk - which I did for many years, only recently finally dedicating an office in the house.3.

Who cares if it cashflows or not.

It might be a good deal but be careful.