I noted the year-over-year increase in STR permits, the decrease in average nightly revenue, and the sentiment that economically-incentivized sellers would flood the market after this winter season (effectively increasing housing supply and decreasing prices).

No need for all of us to learn the hard way when you guys have figured it all out.

You're no longer married in 2023 (congrats!)

We listed both buildings in a single listing to sell together,  but after a few months and no dice, we decided to list them separately at a lower price.  

BMO Harris allows multiple business checking accounts for Series-LLC's and there's no limit to the number of accounts.

Wanted input on how much might be involved here to remediate, and what range of costs I am looking at, I fully understand that once the drywall is cut open there might be who knows how much damage to the framing, insulation, and whether it is worth it to even get involved with this property.

More units = more options :).Its supply and demand.

No fear of the Big bad IRS wolf coming knocking for a pair trail? 

Of course, no response. 

Buy & hold investors may consider lower cost areas like Aurora, Joliet, SW Chicago, and others to get a balance of cash flow while still investing in a decent area.