Are there any benefits I may not be aware of here? 

I would recommend getting a free cost/benefit analysis to see if you specifically could benefit from the study.Real Estate Professional Status

Its time to get an accountant who specializes in real estate taxation. 

Focus on tax-saving strategies such as cost segregation studies and bonus depreciation to accelerate deductions.By qualifying as a Real Estate Professional (spending 750+ hours annually and materially participating), you can offset your wife’s S-Corp income with real estate losses, reducing your tax liability.

One of the other factors that kept me from pulling the trigger is that the city has never passed any real STR regulation.

Not unless she adds more real estate work.C.

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. 

@James TobinJames, congratulations on deciding to take the first step into real estate investing!

For long term, the main benefit is having someone else pay off the mortgage on an asset while you collect cash flow.

It will familiarize you with the basic terminology and benefits.