I'm just not seeing any strategy that can offset to any significant degree, the depreciating nature of either asset.  

It worked out well, but not without its challenges, and I learned a ton along the way.How to find a partner: Meetups and forums like this are great places to start.

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Without knowing the nature of your partnerships it’s tough to say specifically.

The challenges in real estate teach you invaluable lessons that you might not gain otherwise.I also invest in Chicago, so I have a few thoughts in response to the questions you raised.

You haven't even asked about your BIGGEST challenge - finding "trustworthy" contractors.- Most contractors will cut corners, or worse, once they figure out they won't be watched closely:( Your job will also go to the bottom of their priority list.Monitoring progress is relatively easy: hire that same inspector to go by weekly or before any payments to take a VIDEO of:1) What was done2) Quality of workmanshipOne other thing you didn't ask about, payments to contractors.- They all want 50% down or as much as they can squeeze out of you. 

What pitfalls or challenges should I be aware of when scaling up quickly?

2024 will go down as, "The Year of Taking Action".Getting back in the game came with some challenges.

With your background in lease management and site selection, that could be a natural next step.Regarding STRs, I can understand the hesitation—accurate expense tracking is critical, and not having that data can make evaluating deals frustrating.

Challenges?