Quicken in my experience can be somewhat difficult to work with throughout the process (as most online lenders are), and as such many list agents won't "sell" your offer to their clients as well as one with a local lender they recognize.Definitely go with the conventional if you qualify, your offer will look much more solid, you won't be stuck w/ PMI for the life of the loan, and its only 1.5% down more.Your budget is going to be stretched in Pilsen, University Village, and Little Italy for a 2/3 unit, unless you get something dated and in need of rehab.

Im posting this unique deal.

This particular one was a very unique offering in our area and I felt 10% was well justified if I closed fast.

It was supposed to be a short term deal that stretched out to a 10 year headache - complete with difficult tenants, difficult partners, and hidden construction that I unearthed when I was preparing the property for sale.

It was supposed to be a short term deal that stretched out to a 10 year headache - complete with difficult tenants, difficult partners, and hidden construction that I unearthed when I was preparing the property for sale.

It means that not only is it rare, it’s unique and genuine.

Everyone's situation is unique and thus your CPA and Attorney will provide the best answer that meets your specific situation and desires.

@Jamiel StricklandYou're denying the unique growth of West Village by lumping it in with "downtown". 

There are several reasons for this, but I think the biggest is how far your money can stretch with the down payment requirement for each.Your motivation for wanting to invest out of state is the lower prices, which I certainly can’t blame you for, but here is the issue with that:Say you’re looking at purchasing an OOS property for $170k.

I don't trust to give the code to a prospective tenant; even if we install one with unique codes, you still have to worry about them messing the house, or leaving the patio door open or window open and coming at night to steal stuff, and you'll have no idea which one of the visitors is at fault.