Your response really helped me understand the key aspects of short sales, especially regarding title issues, lender valuation, and inspections.I truly appreciate you taking the time to share your expertise!

However, should you have net rental income that is subject to net investment income tax, then REP status would be helpful to avoid NIIT.Just to be clear, if you have an STR and you materially participate in it, you aren't subject to NIIT. 

We sometimes get buyers who have highly unrealistic expectations on performance, ease of self-managing and other aspects of owning the home. 

Because it takes "an expert" to explain novation, avoidance of due on sale clauses, ignorance of state foreclosure rescue statues trusts, why you don't need title reports, attorneys or reserves, and don't forget to throw in the Garn–St.

I’ve heard from many (non-experts) that I’d need to stay for at least 5-7 years to avoid taking a significant financial hit, but that feels like a waking nightmare given how much this issue affects me.Financially, renting it out isn’t an easy solution either.

Owner only gave us $2k to work with, so we took care of Health & Safety issues (to avoid lawsuits) and did our best to spread out the rest to make the property look "decent".

An expensive fix that could've definitely been avoided

We also tell them that we charge $25 per hole for TV mounts, shelves etc I think that $10 up-front investment has reduced the number of issues by probably 80%.Our walls are textured (sand textured in Milwaukee, orange peel textured in the western suburbs - yes, there is an actual dividing line), so we try to avoid the usual palm-sized patch and fill only the hole without making it bigger, so we can get away without texturing.

Typically, I avoid using a series LLC in Illinois because each cell requires state registration.

If you are having a lot of interest and you are trying to avoid multiple showings that take up too much of your time.