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?

Hey Michael, My understanding is in a preferred equity syndication, utilizing qualified funds such as those from an IRA or 401(k) can trigger Unrelated Business Income Tax (UBIT) when the investment generates Unrelated Debt-Financed Income (UDFI).

I’m not sure when to decide that I “know enough” to make this kind of investment, or if I should continue educating myself before pulling the trigger on a 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.

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). 

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

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.

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

However, all strategies, tactics, etc TRIGGER the “due on sale” clause, despite whatever people selling “how to” ideas want you to believe.