When leveraging money, I think it makes more sense to do it in a market that’s showing signs of growth.

I went to his preview event today,  where they give you some basic info, and try to get you to sign up for there 3 day course for $997.

You also get free credits on sign up to try them out.

Cover the boat and/or put a "NOT FOR SALE" sign on it and go about your day. 

If the guidelines are clear before they sign the dotted line, there is a mutual respect, and a good vetting process is performed I think I can minimize tragedy.

I briefly considered signing my STR over to an arbitrage group last year under much less favorable terms last year.If this suites you it may be advantageous.

The people trying to sell a 40k course likely told it's easy sign people up for it and you get a cut etc. and make big money.

The snippet you provided is a bit ambiguous which may itself make it unenforceable.I think your goal should be to get a signed doc from the parties to the agreement saying an STR is permitted under the agreement.

Lenders and appraisers may see this as a sign of a room-by-room rental setup.

Sometimes they find a renter that will sign a lease for a high amount only for the renter to default leaving the owner eating the vacancy.