Banks can refinance a rental property under an LLC, but it sounds like you would really benefit from investor-specific consulting and lending.

Market Analysis: Palm Desert seems seasonal, so the cash flow challenge might not improve significantly without some adjustments.

One of the side benefits is that I can avoid the whole draw/inspection process (not overall inspection, just the ones tied to the draws) and don't have to worry about draw fees.

Larger owners tend to analyze market rents monthly or even weekly and manage rents (or incentives) the best way they can.As long as the owner is engaged, the chance of adjusting rents is higher.

If they get married it will help her earn SS benefits, etc etc. 

Consider using an FHA loan to secure a 1–4 unit property with just 3.5% down and take advantage of tax benefits by living there for at least two years.

There are plenty of STR-savvy CPAs who can help you navigate the rules, maximize tax benefits, and make sure everything is done right.

I'm just here to note that an LLC does not offer a single tax benefit, nor does it allow any deductions that aren't allowed without an LLC. 

And the real benefit of real estate that makes it worth the hassle is appreciation.

Quote from @Dean Sexton: There are benefits to both options.