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

Thank you so much @Greg O'Brien, I just bookmarked this thread, I stayed up until 2am last night trying to find answers to this, confused by different professional opinions and IRS publications.I'm trying to use STRs (rented out 7 days or less with no substantial services provided in which I materially participate) to reduce my W2 liabilities and my biggest concern was if doing this will trigger Self Employment taxes.If I understood correctly, in this situation I can use depreciation losses as active against other active income (which is what I want).

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.

Follow the grey-haired people with life experience and real wealth instead of the flashy YouTubers making money off suckers. 

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.