I'd encourage you to keep metrics on everything so that you can see your KPI's evolve over time.

So to count on scoring one of those in the small window for a 1031 would be tough.Should I just keep the property, do light reno's and increase rent and bank cash flow? 

It's absolutely essential to keep learning, so I applaud that a lot.

That means you might have a refi clause but not have enough equity to refinance. 

We actually keep marketing a property and accepting back up applicants until a property is actually occupied.

If you keep raising rent the max allowed it may take some time but eventually you should end up high enough that they move. 

I am not sure I buy that Pilsen is the one southside of Chicago neighborhood driving rent increases, but it is surely a gentrifying area and factor.I think Bronzevilles & Woodlawn's ability to have more new developments has allowed that entire se coordinator to become a huge factor on the southside.Regardless, whatever you are doing is working so keep doing it!

I’m having a hard time deciding if I should move forward with the deal or keep renting (currently paying $2200/mo in an apartment, we would have to pay $4k to terminate lease early).

Step one know your FICO score, keep it high.

They're still trying to keep their machines at my four-plex saying that it's now month to month then saying that the previous owner suspended services so that time doesn't count, but won't provide any dates.