If both the mortgage and title are in your and your wife's names, setting up a multi-member LLC with both of you as members might help avoid triggering a property tax reassessment (some counties do that) since it shows continuity in ownership.

If you receive any boot (like cash or non-like-kind property), then some of that recapture could be triggered and taxed.

Some questions I ask myself before pulling the trigger:1) In 1 year, would I make at least double of what I invested into this- or any- coaching program?

This is in FL and the lease says "We will not be liable for any damages, loss, or injury to persons or property occurring within your dwelling or upon the premises.

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

(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). 

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.  

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.

Columbus is the other market on the list that we are familiar with and would pull the trigger with boots on the ground.