I would bite the bullet and do the expensive one.

We ended up having to get our first tenant late in the season.

Interested in meetups (when this social distancing lightens up a bit) in the Washington DC and Northern Virginia area to connect with seasoned investors and explore if I can find deals in the area.

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.

Ok I wrote those out as bullet points but it looks like they didn't show up that way.  

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.