But, based on my understanding from the accountant, the fundamental issue is that the IRS considers it as a 1231 sale because it is "rental real estate", and as such, it is considered "ordinary income" (with some consideration for depreciation) - this is irrespective of holding period.It seems a bit strange/wonky to me, but I am no expert on taxes and the IRS code.

The program is fundamentally based on making money out of subject to deals and wrap arounds that are about to become illegal in Texas. 

@Addie Burchell first off, your starting with a fundamentally flawed framework, so as they say GIGO (Garbage-in, garbage-out), as in you will never get a correct output answer as long as input framework is flawed as it is here. 

While this is real estate, it’s fundamentally a hospitality business, and that’s what makes it thrive.

I think the fundamentals remain the same, have reserves, know your market (laws, seasonality), costs to operate (vary greatly between long and short term) and have a multiple back up plans you can pivot to if needed.

The underlying fundamentals in Chicago are very, very stable.

The pricing in the book is outdated now, of course, but the fundamentals are still there.

Usually strategic locations suggest good fundamentals which means you are in a neighborhood where you wouldn't have to rely on section 8 tenants.

@Charlie GreenwoodCongrats on breaking the ice and welcome to BP.Ogden may not have the cash flow that the mid-west markets do, but it has better fundamentals.  

That being said, I do believe in the fundamental American ideal of rolling up your sleeves and doing the hard work yourself.