Hi @Jacob Dalton,Thanks for sharing your situation—it’s clear you’ve put a lot of thought into this decision, and I can understand why you’re concerned given the challenges of being a landlord in Cook County.Screening tenants is definitely a key step, but I agree it’s not foolproof.

.🔹 Insurance Challenges – Even when insurance pays, it rarely covers the actual cost to completely rebuild.

I wasted too much time trying to piece it all together and when you're in different states it's all the more challenging to make sure everything is legit.

The original post leaves the door open for a challenge by the IRS, so the safe harbor of holding it for investment for two full years is the safer option.  

." - which to me indicates the same doubts that I have about the legality of the IRS position.Until the IRS is challenged in court over this position and loses, I choose to comply with their position.

Back in 2018, we encountered one of the most unusual title challenges we’ve ever faced while working on a multifamily wholesale deal.

Challenges?

When I return to the country after my Au Pair contract ends, I hope to live in the property as my primary residence and house-hack as well.I understand that investing remotely makes things more challenging, but I am also ready to be uncomfortable and challenge myself in this journey as I know it is 100% possible.

Attend seminars, join online forums, and read up on the latest market trends to stay informed.Remember, real estate investing is not without its challenges.

The increase to expenses has been a challenge.