Same as @John Underwood, @Diaz Principe Nicolas.I would love to get more off season bookings but there ins't much call for a iced in lake house with a foot of snow on the ground and the lake being frozen over.It is fun to see how many turkeys end up on the deck and to watch if wolves use the frozen lake to move around.

The reason it is legal, with some assumptions, is that the person engaging in it is a principal acting on their own behalf.

It's crucial to carefully evaluate the benefits, drawbacks, and costs associated with forming an LLC and consider how it aligns with your overall investment strategy and goals. 

It depends on where you are on the investing phase, everyone will be in a different part and have differing opinions.I was in the growth phase a couple years so I looked to take on more debt to build my portfolio.I accumulated a lot of wealth after all the appreciation over the past 5 years.I am now looking to decrease my debt.Once the debt is paid down, I will be able to get an increase in monthly cash-flow that would have went to interest / principal paydown.Remember the goal is a comfortable living situation and not to acquire more rentals(or another job).

The current discussion is that we'll agree on a payment and then "x" amount of each payment (same every month) will go to principal (instead of following an amortization schedule). 

Too complicated and feature rich can be a drawback as well.

The appreciation and principal paydown gained over the years was well worth the shell game I played by under rehabbing the houses for rent to keep under that 70% ltv mark and still offering enough to take them down.  

Keep growing that Roth IRA, as the principals of compounding interest in the absence of taxation are powerful! 

As @Nick Harrington stated the main drawback as I see it is that you are buying at retail or very close to it.

There "may" be a policy form out there that doesn't require this, but all the ones I've ever seen follow these standard insurance principals.