We wanted to help this family avoid that pain, so we decided to loan them $5,000, expecting it to be repaid at closing.At that time, we had about $10,000 in our business bank account, so this loan was significant for us.

I developed a $1M+ house here in Chicago, and it was painful.

Real estate professionals, what’s the most painful or repetitive part of your job that you wish you could automate or eliminate entirely?

@Nazimuddin Basha, There's a whole lot of us feeling that pain of increased insurance costs and resets in taxes. 

One landlord I know told me that this can send a positive signal to tenants that they will likely end up embarassed when facing eviction and it might be best for them to move out on their own.

Cleveland Heights is a pain to deal with.

The seller can provide all the documentation in the world, but you really have no clue if they are making it up or not.The best signal I've been able to get regarding whether or not an inherited tenant is "good" or not is how well kept they keep the house.

And then, from 900 to 1050 in year 2.Smoking is a pain when taking over a unit to turn.

Hopefully the pain abates in 2025 as the onslaught of new supply slowly abates. 

The short term pain you'll incure is well worth it when you look back three months from now.I would start interviewing other management companies ASAP.