Doing HML inside of a retirement vehicle is a great way to grow your funds tax deferred. 

So, both my wife and I are full time W2 employees and are in the 24% tax bracket, and I came across the short-term rental loophole which sounds really amazing for taking write offs and using them to reduce your W2 taxable income, but also equally difficult to qualify for, unless you are within a short driving distance to your property.  

I was wondering if there are any potential tax deductions we could take as a passive investor. 

I see you’re a flipper, don’t have any advice or tips?

LLC or not won’t make a tax difference. 

What I don't understand is how should I think about the tax benefits when holding rental property in an LLC.

I am happy to speak to what I have seen as the most common set up from a tax perspective to give you a starting point for a deeper discussion, but ultimately you will want to speak with your CPA in conjunction with an asset protection attorney because this requires a deep dive into your specific situation.  

It’s heavy manufacturing, finance industry, health care, Tech Giant presence, 3 pro sports teams (and hopefully an MLB team), zero state income tax, and nearly 1100 companies have located to nashville in the last decade.

I'm wondering if he would be willing to accept an offer that has long term tax benefit, I would give him his asking price, the only real problem I foresee in the repayment would be another big downturn.

Nor would I buy here with the looming property tax threat against STR's.