Any thoughts on how I might approach the conversation with them?

I am an agent in the Greater Cincinnati area and if you want to continue this conversation, shoot me a message so I can learn how to help you better

I've had him read some of my books on investing, and we have conversations often about how you can finance (and refinance) properties, etc. 

Your broker may feel entitled to an additional split based on past dealings or conversations with this client.

They sound like regular conversations where the RE professional/investor is genuinely interested in discovering the seller's pain points to help find a solution.All the best!

I had a conversation with a Probate/Estate lawyer and he suggested the following but what he said doesn't quite add up to what I have read so I want to see if I am just not understanding or if I am getting bad gouge.Advice was to create WY LLC that owns all properties, that is then "owned" by a land trust for additional anonymity, that the beneficiary is a regular Trust that owns everything else in my name.

Whether it’s problem-solving on the fly, handling difficult conversations, or simply staying calm in the chaos, these experiences are shaping me into a better landlord—and, hopefully, a better person.Real estate isn’t just about turning a profit.

And let the conversation go where it goes. 

After inspection/appraisal is done, then you do the Padsplit conversion. 5.

When you convert an asset to Roth you have to get a third party valuation and often they come in at a major discount..25-60% so your taxable amount is way lower than the actual conversion.  4.