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.

I would avoid areas with no regulation unless you find a hidden gem.There are still many gems out there specialy in tightly restricted markets.  6 months ago we missed on a property that went up for sale. 

I know there's STR restrictions in LV proper, but since this is part of a resort, I would assume the resort can rent my unit when I'm away?

Its not much of a difference and I would recommend going with 5% down conventional as there's less restrictions when you decide to leave the property and no upfront mortgage insurance. 

The IRS imposes a 20% penalty for inaccuracy when a taxpayer significantly overstates expenses. 

And renting may be cheaper if you factor in taxes, insurance, repairs & maintenance, and closing costs on both ends.Buying can be much more profitable, but it can also be very restrictive and emotionally painful. 

As the local governments struggle to manage tax payer money responsibly, they should really offer incentives to private builders to build "income restricted" at a much lower price. $220-$300/ft for vertical build costs.  

Unlike some states, North Carolina does not impose a state property tax, leaving the determination of tax rates to local governments.