The downside is restrictive guidelines, a ton of paperwork, lack of flexibility.Commercial types of financing have pros that are flexibility in guidelines and structure you can do all sorts of stuff from substitution of collateral to partial lien releases on blanket commercial mortgages to cross collateralization and many others, less documentation than conventional financing products, use of debt coverage ratio (DCR) as opposed to Debt to income (DTI) and if you compare DCR to DTI the commercial lenders go up to 80% DTI since the reverse of 1.25x DCR is .80 or 80%.There are downsides to commercial financing and that is the convenants with in the mortgage note that can allow the lender to call the note so make sure to read all the definitions for what substantiates a "default," by the lender you'll be surprised by the definitions and language at times. 

Is 10k all of your savings or so you have substantially more?

You have thousands of people doing the same thing including major operations that have a substantial  degree of resources on the ground canvasing, door knocking, advertising, and submitting contracts almost around the clock.

The IRS position is that it is the taxpayer's responsibility to substantiate all deductions on the tax return.

.- Risk that prices increase substantially over the next 3-5 years, and outpace any of the benefits aboveLeaning towards selling since it’s hard to pass up free money, I’m not sure prices have much further to go from here, and we’re not sure we’d like to move back to the same home that’s been rented for 3-5 years anyway.

A dwelling unit is not habitable if it violates provisions of housing or health codes concerning the health, safety, sanitation or fitness for habitation of the dwelling unit or if it substantially lacks:(a) Effective waterproofing and weather protection of the roof and exterior walls, including windows and doors.

Was looking at something in Pilsen like this as well: https://www.redfin.com/IL/Chicago/1712-S-Morgan-St...But I guess over my last 4 years away from the area, it's really become a trending area that has increased in costs substantially.

The problem comes that the seller is CAPing the POH rent which can be pretty substantial. 

As a retired techie, I'm fascinated by new technology and its potential applications.I imagine 3D printing technology will substantially reduce the cost to build stuff, which would be deflationary for the economy.

If you're interested in taking a look, there's a lot of equity in the deal.