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.

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.

Did they sign a lease or are they still considered STR?

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.

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. 

I never heard back, but all 7 clients apart from the “whale” client re-signed with me.

Here’s some perspective:1% Rule: Meeting the 1% rule is a good sign, especially with many markets struggling to hit this benchmark.Cash-on-Cash (COC) Return: 8.73% is decent, especially with today’s higher interest rates.

Which would be signed AFTER the marriage takes place.

Some may have you sign something that say you don't intend to live there ever.