Would I have any issues with the insurance company in case something happens?

There is such a supply and demand issue in many markets that low rates will drive prices higher.

I am worried that the house might have had foundation issues before it was flipped. 

Area has no issues with finding tenants.

Put in a set amount at set intervals to minimize losses from buying at imopportune times.Hello James,Thanks for taking the time to respond to my post here - it's at least comforting to know that my Chicago market area isn't the only area facing this issue to the extent it has been. 

From it raining a lot the night before the property going active which brought to light foundation issues hidden behind the pre-existing finished basement paneling.

They can decide that offer #2 came from a contract lawyer and he'd be a good owner in the building since he can help them with legal issues...or whatever random reason they like his offer better. 

The equity potential of course, but mainly I was trying to solve two issues - on one end, the seller was struggling financially and needed to sell her home but investors were aggressively trying to take advantage.

The equity potential of course, but mainly I was trying to solve two issues - on one end, the seller was struggling financially and needed to sell her home but investors were aggressively trying to take advantage.

I use Quickbooks Online and haven't had any issues!