I couldn't find anything too specific on the site.

So, the first question they usually ask a PMC is about fees - instead of asking about services and HOW those services are executed.EXAMPLE: PMC states they will handle tenant screening – what does that specifically mean?

I never go off of a flat percentage on anything, I analyze the costs to get to a specific return I target and analyze the risk that is involved. 70% may be an initial metric to see if it is even worth pursuing, but every deal should be evaluated independently based on costs, time and risk involved.

Mailchimp also I believe is free up to a specific number 

Specific is how I classify loans toed to a specific property, and generic is how I classify our family loan that is not tied to any specific property, so I have to allocate it myself.

STR regulations have been a VERY hot topic here for the last year (and even beforehand).

I mean in general what sort of expert should I try finding first, but if someone has specific people in mind who deal with the UP that works for me too.

If the laws are still concerning to you, then buy a commercial property, like an office or industrial property, in your area. 

One of my first questions is always - "what are your specific goals?"

I mostly agree with Huong, but in specific cases, a small negative cash flow is not the end of the world.