You can usually use bonus depreciation against the asset assuming it will follow the short term rental loophole rules of 7 days or less average stays. 

I'm a developer, hold my GC license and real estate license and we're building duplexes near downtown right now.

You will have to be prepared to foreclose if the buyer doesn't meet the terms of your agreement.

Turning a single-family home into a room-by-room rental strategy really paid off, especially in a neighborhood like Portage Park where whole apartments typically rent for less.The demand for month-to-month flexibility is growing, especially in cities like Chicago, where people might need shorter-term housing due to job relocations, school, or other temporary situations.

My wife and I don't want to follow the scale up construction company model (we already did and it wasn't the best).We do a lot of labor on our projects and are looking in to the future and realizing our bodies will not hold out over time.

Strong mid-long term rentals, with a reasonable flip option?

I self manage and I hold myself accountable to each property's success. 

Most of the content he has posted on IG recently is asset protection and international trusts (trust in the Cook Islands), international bank accounts (in Dubai), etc with videos of his family traveling in different countries.For someone who owns multi-millions in real estate, that makes sense but for 98% of the investors on here, especially new investors, it makes no sense to pay $20,000+ to establish international trusts, holding companies and LLCs for asset protection (from lawsuits) and a tax shelter.

Our weekly short-term rental newsletter covers all things STR here at BiggerPockets!

Would you still hold if you had such a sizable opportunity?