Thank you - extremely helpful!!

I have not pulled the trigger yet on a second property due to risk averseness, lack of capital and analysis paralysis.

They just passed some extreme anti landlord laws.

So unlike markets like 30A and the like where prices have remained rather steady despite the returns being extremely poor at current home prices, I think we've probably already hit the bottom (or at least near it) on home values.

We have written agreements with both and our attorney reviewed both and we know we have an extremely good case in both cases.

(Fannie/Freddie allow you to transfer into an LLC without triggering a "due upon sale" clause, but ownership of the LLC needs to match the existing title of the property). 

Your management has to be top notch, your marketing has to be top notch, your pricing has to constantly change with the environment, your design has to be incredible and the photos have to trigger that booking response.

Now that I'm a more experienced designer in real estate, I would love to customize my kitchen more with different materials, unique tile, and more unique pulls/knobs but having a large, clean kitchen was extremely appealing to me as a first-time buyer 4 years ago.

Since refinancing and investment income (like rental income) usually aren’t seen as earned income, it likely won’t affect your mom’s survivors' benefits.However, if your mom’s survivors' benefits are based on disability (SSDI), then additional financial or property assets could trigger a review, so you might want to consult a CPA or financial advisor to be sure there are no unintended consequences.This isn't legal advice.

This is known as a Roth Conversion, which does trigger tax as you are moving from pre-tax, to post tax Roth.