Seasonally this is a better time to buy and if there's a "Fed pivot" in 2023 interest rates will come down slightly and increase your competition. 

Whether you are a first-time homebuyer or a seasoned investor, here are some of the most important things to consider when buying your first property:Debt-To-Income RatioDuration of stayJob securityDown paymentEmotional stateLocal market indicatorsMortgage ratesSupply and demandMonthly BudgetHope this helps you! 

My thoughts were seasoning period (refi), what types of documents need to be provided, if they finance OOS deals, if they do portfolio lending, max LTVs, etc.

Are there any seasoned BRRRR practitioners who are willing to jump on the phone to advise me?

Maybe offer some incentive to break the lease early as 5 months from now is also October so you're passed the typical "renting season" in Chicago.

If possible, it may be a good idea to wait until January to put your home up for sale in order to avoid the potential lull in demand during the holiday season.

The market is strong, but seasonal in that summer is busy and rates high whereas fall, winter and spring is less busy with lower rates. 

I hope you had an excellent relaxing Thanksgiving holiday and have exciting plans for the Christmas season!!

Need some help from some seasoned professionals. 

Off season a weekend or 2 to 4 days. 1 month or so in advance.Summer - A week, 6 to 12 months in advance.