Before getting on here responded to a messaged saying that this may be an option for someone who fails to meet the identification period for a 1031 but if someone has a large gain they may also have a large amount of recapture... 

But, what if only ONE owner can afford to make a large repair (i.e. replace the A/C unit) after one year and the other owner cannot afford to help with that repair?

In my experience, those large cuts are normally due to findings during inspections from past potential buyers.

In theory if a property can not produce positive cash flow with a hypothetical 100% financing it will never have true positive cash flow, you will need to buy your cash flow up front with a large down payment.

I'm a 34 year old financial analyst from a very large corporation so i'm incredibility comfortable with numbers, analysis, and 95% of general accounting (I still use a CPA for my own real estate properties, but that's mostly to have an expert who's up to date on all the laws go over my numbers).

Now I am hitting road blocks such as LARGE reserve fund requirements for each prior loan in order to secure a new loan.

If it was a good deal to begin with based on the 30-year fixed rate, I doubt the ARM adjustment will be large enough to cost you more on the whole in at least the first 3 years after the adjustment.

@Hae Sun YiThe whole city of Chicago is hard to compare directly to a town like Naperville as far as rent values, property values and taxes because the city of Chicago is so large and diverse one neighborhood compared to another is really like comparing Naperville to another suburban town. 

The neighbor tenant shot large fireworks from his yard directly over into/above my property, and when she walked over to ask him to stop, before she said anything, he threw fireworks over his fence directly at her.

I have rental property which is on a large develop able lot with a shop in the city.