Well, we have no idea what their contract said about insurance but usually the buyer is responsible.

You absolutely want title insurance, many people never do the probate thing completely right.

How much cash you can take out will depend on a few things:Income on the property - if the property is not a source of stable cash-flow, that would be the biggest issue.Strength of the leases - who are the retail tenants?

I sent the $2000 cleanup bill to the tenant for negligence and she is refusing to pay claiming that my homeowners insurance should cover "old pipes." 

60618 seems to be a very stable and appreciating market for mid to higher end homes.

That's gross rents, you need to account for real expenses, like taxes, insurance, PM fees (ours is 9%), etc.

We are hoping Real estate investing will allow our family to transition out of the military to a financially stable future for our 3 children.

Did the new owner purchase title insurance?

Does having an L.L.C. generally result in higher property tax and insurance?

This also results in a discount on my yearly home insurance.