Obviously you'll want to check the math on all of this before pulling the trigger. 

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

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

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.

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).