While it’s not impossible to close in mid December and still meet all requirements of the STR loophole, it will be extremely difficult due to the nature of hitting 150 hours, having it rented for 15 days or greater and having the avg stay be no greater than 7 days and not a decimal more.

That doesn't make them bad, per se, it is just a very difficult market right now. 

@Elizabeth RossFor properties under 100k you will likely need to use the BRRR method as its difficult to get a 30Y loan on a properties valued under 100k.

Nothing is that difficult but there are a few things to know.  

I equated it to a property per year simply because in the Denver area it's very difficult to find cash-flowing deals that make the investment worth it, so I figured I'd be looking at several properties to reach my financial goal. 

The bigger companies like Apple, Google, Microsoft, etc, use RMC's to handle their relocations and they are very very difficult to pierce.

While i was able to get make a few offers, tracking that effort was difficult.

As things get more difficult more and more and just staying higher end. 

Common examples include difficult grading, or an irregular lot orientation. 

The main differentiator that I have seen is: 1) Asset class: Retail rarely even dipped in price and it's difficult to even say that it had a downturn.