We all know about the shiny object syndrome or at least we have heard of it. 

My former journalist self enjoys digging into Colorado laws and counseling my clients on where they can do short-term rentals and under what circumstances.

Is that a correct assessment?

The loan is with you, not with your tenant, so none of that means anything to them - in fact because you live in one unit and it's under 4, if you were self-managing you don't even have to abide by fair housing laws (at least on the federal level). 

We teach you how to self-manage and support you with loads of contacts for your team in each market. 

An LLC shields personal assets from business liabilities, while S-Corp taxation allows you to reduce self-employment taxes by taking a reasonable salary and distributing remaining profits as distributions, which aren’t subject to payroll taxes.

I wouldn’t subdivide based on your objectives.  1.  

Charming, smaller coastal towns with a slower pace of life, natural amenities, seclusion and semi-self sustainability are high on the wish list of many high level clients and investors. 

As far as self managing, it’s fairly easy.

No system is perfect, so don't waste time chasing after the next shiny object.