It is true that certain policies will accumulate significant cash value, but you either have to put in several thousands for a certain amount of years and let it season for a bit (Life Insurance Retirement Plan) or you pay your monthly/annual premium for quite a while and wait until you're in your 60's or 70's+ to have access to a good amount of cash value (Variable Universal Life).

I'll for sure need an architect and lawyer amongst other players.

We‘ve also been considering the idea of going to short term during the summer season and keeping mid term sept - may.

Since I'm approaching the stage where I'm looking around for a builder what are your thoughts on working with a seasoned rehabber that wants to get into GCing new construction?  

Is that income seasonal or long-term stable?

Always good to work with a seasoned rep who is reliable well respected and has aggressively priced products. 

Posting on random/obscure booking sites will probably only account for 1% of overall bookings. and the vast majority will come from the big players (Airbnb, VRBO, etc). 

Drive around off the strip, out of season and what will you see? 

Think about if a seasoned syndicator of multifamily is having challenges than what about all the newly trained up syndicators at these workshops that bought marginal properties massaging debt to get investment so they can make money?

@Michael Baum also hit one of the most important things - dynamic photography that changes with the seasons and mixes itself up so it's not a stagnant listing.There is no hack to be the best at something (just look at all of the number one bestsellers on Amazon who sell 100 books total), just work on the product, the amenities, the dynamic pricing, and be resilient and responsive to feedback from the first guest on.