-Time-Money-Knowledge-Coach/Mentor-Fear

Are there business coaches out there ?

The hardest part of the transaction is explaining the mechanics of the deal to the agent...but once they learn they are getting their commission they are willing to learn....seller carried deals work exactly the same as a normal RE transaction...so, they already understand how it works...they just need some coaching and encouragement. 

The fact that she states that it's all "above board".... but yet needs to coach you on "what not to say" should be a red flag right out of the gate.Yes, many municipalities are clamping down on STRs....and unfortunately it appears to be true for your specific location.

Choosing to use a mentor/coach trades some membership fee or training costs for speed, access, experience, and mistake avoidance.  

More for the passive investor but I like The White Coat Investor podcast and ChooseFI (financial independence).Inside Strategic Coach by Dan Sullivan is a good one for business imo.

I won't include links to a website where I upsell a forms package or coaching.

I have followed those guys for a while but can't justify spending that much on coaching.

I am not part of the coaching/mentorship but also looked into it.

It will be a lot easier if your lender can act as a coach for how to best use debt as a tool to scale your portfolio.