If this is an investment property it is going to be much tougher to get a HELOC due to the LTV restrictions.

And even if so, I'd imagine there would be LOTS of restrictions and red tape as to what you'd be allowed to build and its appearance - No?

Once the new pit is installed we’d install aproper vent to restrict the sewer gases from getting intothe home.

I can use a VA loan to purchase a house here, then use my wife's VA loan to purchase a house in another market a year later if not DTI-restricted.

With a minimum 30-day rental period, tight registration criteria limited to permanent residents, and associated compliance costs such as fees and taxes, entering San Francisco's STR market without first examining these restrictions may result in problems and severe fines.

Are there any weight restrictions along the way (i.e., bridges)? 

If states and counties implementing new restrictions on use of the property, I would advise against this. 

Many lenders have policies in place that restrict or prohibit transferring a mortgage to an LLC, especially if the property is not your primary residence.

But in looking at HI I'd be careful of three things.1. new legislation prohibiting or severely restricting short term rentals in the works.2.

Lenders may have specific requirements or restrictions for loans to LLCs, so it's essential to consider how this might affect your future financing options.Before forming an LLC, it's crucial to consult with a qualified attorney and tax advisor who can provide personalized guidance based on your specific circumstances and goals.