My (meanest, but) best tenant is not particularly sophisticated, but has rent scheduled as a recurring auto-payment, God bless her.

All of the examples in the book and practice problems typically revolve around multi-million dollar properties, so it does require some level of sophistication. 

I am a sophisticated investor considering an investment with a syndicate.

If you get that answer in writing expect it to cost more than simple verbal responses.Also, internet research of certain terms may be useful, but realize that the legal definition may be different, and also may be location specific.Making a list of questions, and talking to an attorney about them all at once might prove useful--but remember he/she is on your time-clock/payroll, and huge list will probably cost more than a smaller list. 

I tend to like a less sophisticated broker or agent that just happens to get a seller on a big property listing.

You need to account for on-site payroll & a management company (unless you are set up to manage yourself).  

@Rhett Tullis Typically, with large assets the management system includes a property management company plus on-site pay-roll personnel.  

Any profit went to the more sophisticated seller. 

If it's automatically categorizing the mortgage payment, then it sounds like it doesn't do that, unless it's really sophisticated and automatically calculate how much is interest and how much is principal.

This means there are fewer and fewer tax professionals out there to handle tax clients that are becoming more and more sophisticated (QOZ, Crypto, etc).