How many lawyers did you consult with?  

Consulting a CPA is a must to navigate these nuances.Double-check these details with your lender and CPA to avoid surprises and keep scaling smoothly.

That said, $8k is a big nut so I'm really not quite sure if I will go with a private consultant on an hourly basis or go with them or some other form of coaching.  

I have 4 STRs including 2 for 25 years and I consulted the co-host for local cost estimates.  

If you’re unsure about their response, consulting an attorney or contacting the CFPB may help clarify your rights further.Hope this helps

Should I offer to pay them for their consultation, or are these types of questions common as part of the PM vetting process and is a "courtesy service"?

This ensures your books match the timing of your taxable income.It sounds like you're off to a great start—make sure everything is categorized correctly and consult a CPA to confirm your setup.

Should I offer to pay them for their consultation, or are these types of questions common as part of the PM vetting process and is a "courtesy service"?

I think he has a free consultation as well.

In new markets, network, use a trusted title company, and consult an attorney for legal guidance.