There is no free ride.

To expand on what @Michael Plaks stated - yes you most likely can do a 1031, the next question is you should be asking if you should do a 1031.It isn't free to do a 1031 - you don't want to spend $2k in fees to have a temporary deferral of what would have been $4k of tax. 

We are leaning towards bringing on a hard working administrative assistant to lighten the load and free up more time to focus on more pertinent tasks.This will be our first hire and are wondering what the best way to go about doing so is.

Please check out the book I co-authored called Lend to Live: Earn Hassle-Free Passive Income in Real Estate with Private Money Lending published by BiggerPockets.com/lendtolive.

.), ask tons of questions, and figure out how to hang out with people who are doing what you want to do (add value, work for free, do anything to get that experience.What area of Chicago are you looking to invest in?

or even not-for-profit online class would be beneficial.

I don’t know if it would be worth it to do a 1031 after only a year unless you’re buying both properties for much less than their worth assuming 10% in selling costs (which might offfset any tax savings over just selling the contract) if the property goes from $100k to $110k by next year your taxable gain will already be zero after selling costs.if you plan to sell soon anyway  I think I’d lean towards just selling the contract and freeing up the money, saving loan and interest costs.

You may even end up living for free or at the very least pay very little of your mortgage compared to if you went out and rented an apartment.

It has so much to offer.Jacksonville community, feel free to share your contacts.   

Feel free to DM me for a few references if you don't currently have any!