I have 2 thoughts for you since you are starting from scratch.1) find someone you trust that is currently doing what you want to do and flush it out with them.  2)You should know pretty quick whether real estate is your flavor or it isn't.  

Firstly, because thee SHF index only track properties that are financed by a mortgage so they don't represent the whole market (SHF is the Fannie Mae / Freddie Mac equivalent of Mexico).As you know, Mexico has two distinct real estate market:A.

Again, these questions have a bit of turnkey flavor to them, but they work very well when interviewing management companies.

Andrew a quick clarification here....there are actually two related and distinct categories of units listed within City of SD; Companion units and Junior units....While the Junior units do require owner occupancy, the Companion units regs do not list that as being required.

I'm not completely sure what you mean in your distinction between a GC and a restoration company.

In other words the issues you're going to confront are going to be distinct from someone who's been doing this for 10 years, or someone who's a totally different market or something else.To me your concern is one of like do I even just get started.

So I'm not sure what distinction he's making.

However, the distinction between rental properties and primary residences significantly impacts your taxes.

@Morgan HopperThere are 2 distinct areas in the Lake Tahoe basin for STR. 

In Tampa we have two rather distinct submarkets, basically urban and beach.