I'm taking all accounts with me so in terms of my cash flow I should be fine, but Fannie and Freddie are mindless robots who do not color outside the lines.

If the fence, carpets and yard are all ill kept then potential buyers will not want to step inside, if they do risk going inside, the gaudy colors on the walls will be unattractive to most buyers.

On the other hand, if you show a willingness to help improve a block or an area, the city can also be a very good friend, too!

Well, a standard sale contract is a good start, most will have a block to check in the financing section or you can add, "taken Subject To Existing Financing".What scares me a bit is your knowledge of this strategy and you selecting it as the way to go.

You could block off only the days you plan to be back in chicago, and literally manage the building with your phone.

Thanks @Ray Rex, that definitely provides a lot more color.

If you are handy it would be a good idea to find a licensed plumber and explain your experience and see if they will allow you to do the bulk of the labor.also with pex in visible areas use rigid pex also color code in red/blue (very impressive to people looking at it), for your heat make sure you use one with an oxygen barrier for heating systems.  

I am in the process of purchasing my first home and would appreciate any guidance relating to knowing how to handle multiple-offer situations, what's a "good" worst case scenario, and if i'm blinded by rose colored glasses. 

I'm sure the small specialty shops, the title company, the brokers can iron out most things in houses and small multi family, some 12 unit block. 

Buy the pump, get a 55 gallon plastic drum, cut it in half, drill a bunch of holes in it (big holes), dig a big hole in the ground in the crawl space about 6 inches deeper than the half barrel, pour 6 inches of gravel in the bottom, put the barrel in, pour gravel around the sides, set a solid concrete block in the bottom, set the pump on top of it, run your hose downhill of the house, plug in the pump and test it out (use a hose to fill the barrel).