When I asked her to write up the offer as soon as I got back from the hour-long Drive visiting the place by myself, she didn’t write it up till two days later, after twice texting her about the offers.  

If you found a new renter to move in a month later, you would still have three months of rent remaining that should be refunded to the departing tenant.

You need to either save money from your cash-flow for your next property, improve the property through a rehab, or PRAY for more market appreciation or at least that it doesn't go down so you can refinance out some money later on.

The value add came one year later, when I converted from long term rental to Short Term Rental.

Thanks, I'm trying to learn what those different rules would be that way there are fewer surprises later. :)

They'll put you into an ARM loan, but you can refi out of it later.

Texted her again two days later, no response. 

It's just so important (at least in my opinion) to get started sooner than later - compound interest is no joke and definitely makes a huge difference in real estate.Do you have any idea where you want to start looking in Chicago? 

A week later, they say they couldn't find anything else and want to sign.

I have even responded and had another bulk message come back on the same number later.