When a property is sold it triggers an inspection to get the property up to code.

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. 

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?

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.