One theory is that the investors see population increasing in these areas and are willing to deal with the ridiculous local laws This actually isn’t even necessary true, the placest with the biggest per capita housing production or “investment” is in the sunbelt, the expensive cities produce a shockingly low amount of housing, obviously zoning laws play a huge role in that as well, but even when you looking up institutional investment in existing properties it’s mostly in the sunbelt, most people who own big buildings in hcol areas just bought them decades ago when they were much cheaper, even D.C. has has like a 4-5 fold increase in value in some areas in the last 15 or so years.

I look forward to reading all of the productive and helpful posts you and others have posted as I believe in becoming the best investor and property owner possible.

Like everyone said.Grab up @Avery Carl's first book - https://store.biggerpockets.com/products/short-term-rental-l...Then grab her next book which is available for pre-order - https://store.biggerpockets.com/products/smarter-short-term-...Seeing as you are new the STR business, these are great books to grab up and read.

Buying distressed & fixing yourself gives you the full intel on the quality of your product, buying 2 rather than 4 you can pay for better locations, then having reserves gives you a healthy peace of mind.

If you find a lender/mortgage broker that communicates very well and in a very time efficient manner start there to see if they have a product that works.Most of the lenders we have worked with in the past we have done multiple loans with.

Looks like you have a solid plan, compound interest will take care of the rest.Can i ask what mortgage product you intend on going with?

Increasing your construction budget by a small amount can have an enormous impact on your overall construction budget, productivity and site safety/insurance premiums.

These may be the easiest because if they are new constructions or full gut rehabs, you can see what the final product value is, and what these developers are buying at.It would be a good skillset to have to actually understand renovation and build cost. 

The goal is sell a product, a venue, a strategy, and everything in between with some responsibility.

Typically a holding company is used for large companies like walmart - who has a shipping/transportation company, a real estate arm, the arm that sells the products etc.