@Austin Farsai Hey Austin. -- this is just the opinion of someone who's done a lot of research and works in a related field.
LLC upsides - the can limit your legal liability if you're sued
LLC Downsides - you have to keep all of the money total segregated, they increase your operating costs and complexity, they increase your costs to borrow, they can be legally challenged and pierced - particularly if you make any miss steps.
Umbrella Policy - it's cheap to get a large commercial umbrella policy, and it keeps your operating model simple (with everything under your name). I'm looking into whether trusts or an LLC makes more sense as I continue to grow my portfolio, but it didn't seem worth the complexity with less than 10 properties.
-- I don't have an opinion on the tax aspect of things. I've been unsuccessfully looking into ways to reduce my active income with a passive business, but it looks like you're on the way to becoming a RE Professional! (best of luck with that).
-- If any attorneys think my comments on LLC are off base let me know. I talked to a lot of folks at this point and haven't heard a compelling argument for going with an LLC over a large umbrella before you've hit the freddie/fannie ceiling on 10 mortgages.
Best,
David