And this is exactly why I say qualified demand will be less, in bold. 100% the reason.

If I don't rent from July to September, all the qualified candidates will be gone.

There are tons of qualified folks in Chicago that know the game. 

Although cash out refinances or second liens typically carry a higher rate of interest, the advantages of a lower LTV purchase can greatly reduce the qualifying interest rate.

Or, you can buy in an area where incomes are higher, crime is lower, and more qualified buyers want to live there, but then the cosmetic upgrades leave no margin (almost every owner-occupant is willing to repaint and refinish floors over time).  

I am looking to purchase another primary residence after my 1-year mark however, I was wondering if lenders will be able to use my Airbnb income to help qualify for my next purchase?

With current inflation, student loan debts and other burdens most Americans can't save enough money to put a down payment on a house and qualify for a loan.

In my opinion, who cares how many unqualified tenants are attracted if I am able to attract a good qualified tenant readily.

Do you have the credit score and credit capacity to qualify for conventional financing?

There is a cost to doing an 1031, the Qualified Intemediate could charge say from say $500 to $2,000 or more.