Even with a traditional FHA, you can be in for as little as $3,500 (3.5% of sales price), with you negotiating for the seller to pay your $2K of closing costs (this is a standard buyer request now), and having your brother on the loan just entangles things and encumbers his credit.

For example if a suit is won against the LLC due to activities involving the business itself the perhaps the judgment would only be able to be executed against the LLC and it may be more difficult to use co-mingling to come after me personally since the LLC benefitted from the loan in my name in the sense that the loan in my personal name could be clearly demonstrated as a contribution to the LLC since the LLC needed such in order to purchase the property to begin with.The very best alternative to all of this is to whenever possible own the property in a retirement (roth or traditional) account as that provides the absolute ultimate protection in America. 

You will be met with skepticism from critics who practice traditional financing usually real estate agents, attorneys, your friends family and the like.

I am new to the site and I am currently exploring options for non traditional financing.

Didn’t go the traditional yellow postcard route or picture of a house.

In fact, based on the fact you don't have traditional W2 income, I think you should be looking for a commercial loan (from a portfolio lender).  

My current financing plan is to use traditional financing since 20% down isn't an issue and both of us have good (700+) credit.

We can't buy with a traditional loan for another 7 months because my boyfriend's job switched from 1099 to W2 the year before last.

A lot of traditional analytical templates, p&l sheets I found online don't really factor in some of the unique nuances of short term rentals like this.  

This has the potential of being a 12 month rental, but not in a traditional vacation rent way. i have been told that a lot of the local and seasonal vacation employees  need places in the off season.