So, get a number of estimates and compare them to find the great deal.

Louis and it would be great to compare notes.

I try to do as much of my homework as I can before asking to see a place, ask for realtors comps to compare with my own, and make a reasonable (yet sometimes it is considerably less) offer.

You really can't compare to what people got a few weeks or months ago.

One of the best ways to tell if it is a good idea is to look at comparable rentals.

My understanding was that you used the cap rates of recently sold comparable properties in the area to calculate the value, and deductively, your offer.

IMO for or someone like @Michael Blitshtein overseas this is a much more reasonable method to deploy his available 30 K across  5 or 6 diverse investments and reduce his risk and management headache vastly as compared to one 30K D grade property.

That's very affordable.You should be able to check comparable rents on-line to find out what rents you could reasonably get for those two units.Regarding legality of two units on one parcel of land, check with the local Building Inspector, or Zoning Board.If it wasn't a three-hour drive from me, I'd buy it.

I have called a few major insurance agencies (Farmers, MetLife) and so far the quotes I am getting sound fairly outrageous, at least compared to what I am seeing across the site and my expectations.What kind of rates are Chicago investors seeing for multi family apartment buildings, and what agents/companies are you using.  

They will also provide you w/ information to evaluate a property (Comparables) Establish multiple relationships w/ wholesalers Establish a minimum profit criteria- The right property is the one that meets or exceeds your profit criteria