I did a similar thing, instead of a GC, I was an engineer  already in the land development environment and put together my own group to purchase land, entitle, develop, etc. 

This is because I realized that it's mostly about cheap all-inclusive resorts you can't compete against and all short-term renters I met across the country hated Punta Cana for that very same reason.

I love that you rented two of your bedrooms as mid term and short term rentals and made enough to pay for the mortgage and now you are going to use the rental income to show you can qualify for another property.This is an excellent strategy and one more people should consider doing in this inflationary environment to offset the biggest cost in their budget--housing.As you rightly point out, you can use this strategy with every house you buy accumulating a portfolio of houses that you originally started out living in as a primary residence every two years.Well done and more people should consider doing the same, or rent their garage, or shed, or a boat, or an extra car.Love it!

In my opinion Option 1 could be a bit risky in today's environment as we are not sure if prices have hit the bottom yet, there are positive signs in the CoS market that point to price appreciation in the future, but there is a good chance the interest rates are not coming down for a while, which will have a negative impact on home values. 

.- I've been on the sidelines with this weird high interest rate and volatile environment for about two years now.

I have two units up (out of four) for lease renewal at the end of July. These are the only units that currently do not pay utilities, which amounts to about $250 per month per unit. I included utilities in the new re...

People have to really put in the extra work for their clients right now in a low inventory environment.  

We are in a Tough environment.

The current interest rate environment’s impact on HELOCs will offset any potential benefit very quickly.

This isn't inclusive but should give you a good start.