We run into this especially at out parcels in grocery anchored centers, and our users generally can't make a ground lease work for the business case so the next best thing does tend to be the BTS or we often do Reverse BTS deals where the majority of the building design and management etc is done by the tenant. 

Quote from @Wale Lawal: @Paige GardnerYes, this strategy is possible, but it comes with risks that you need to manage carefully.

Now have a portfolio of 6 properties with some that are owned others just managed but turn key operation for sure. 

You can hear real-world examples of how others have built their investment portfolio and (hopefully) learn to avoid their mistakes.4.

I have a short term rental that I self manage and am considered a real estate professional based on material participation rules.  

I own a MTR management company in Los Angeles, currently managing 27 properties.

But let’s go a later deeper - my down payment would come out of a well performing stock portfolio.

I have 0 experience managing STR properties, but lots of experience using Airbnb from my travels 😅 I am halfway reading Avery Carl’s book on STR.

Hi Michael,It’s great to hear about your interest in growing your commercial property portfolio in the Chicago area.

Happy to help if you need more guidance, my partner and I have a portfolio of STR's in the area.