Once you become more established, have a large net worth, etc. you may want to consider more sophisticated trusts that can cost you up to $45,000.

I think this is the gift and the curse of a still emerging asset class (short term rentals) - as it becomes more "institutional" i.e. more like commercial real estate with more sophisticated buyers then financials and systems for this will likely become more streamlined and stable, but we are still in a place where the buyer pools are more newish investors or typically residential basic investors, so not has experienced or sophisticated evaluating investments based on a detailed financial analysis like more seasoned commercial investors likely would.anyways, just a guess on what might be going on here

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.

Reg D 506(b) allows for unlimited fundraising and up to 35 sophisticated investors.  506(c) requires accredited investors.  

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.