Seems almost too good to be true…. looking for any downsides and/or wondering if I’m missing anything. 

@Candice ChenI would passThere is no upside for another 8 years and only downside on the maintenance of the property.

It sounds like you are willing to roll the dice but keep the downsides on your next project . . . and assess if Chicago is the right location for your renos.

.:  Hi Jacob,You seem like a newbe at this.If you can find this square space you can slip a bathroom into it.If you can find a space 6 inches longer, and your renter pool has a lot of overweight people in it, you can opt for a 60 in x 36 in shower pan setup to keep them from bumping up against the walls.Also you can easily put in a bathtub if you think you renters would rather have that (small children typically) .With no bath you may turn away renters with small children--It's unpredictable, but I think a big shower makes the space feel bigger, and with the flexi hose wand part, ladies can comfortable use it instead of a bath--although for some you may have to point that out.So for a shower, there could be downsides, with a bath less risk--that's your call.I put in a storyboard to help you think about it better.Also I swapped the window for a bathroom type window.Many say windows in a shower can be problematical, but you have one now and when showing the unit in other than winter, having that window open makes the bath feel fresh, and a surround would cover the old window.

C-corps have downsides of course, but if tax savings is one of your goals, it may be analysis you want to work through. 

The bank is just covering their downside in case they have to foreclose.

The downside with this approach is properties with basements are very rare in the area.Option 3.

Well done on passing on the lower quality rental tenants - I have found vacancy is cheaper than a bad tenant every time (damages/eviction/etc.)On your question about listing it as a flip - you can note that property is being sold as-is, but the downside is some people will think this equates to big investment and you may not sell at your optimal price. 

Understand your downside risk.  .       

What are the downsides to mobile home investing?