@Micah HuffmanFrom what you have said here, it sounds like you have your hands on a very good investment property/opportunity.

AI is not some magical, all-knowing miracle that can pull leads out of thin air.AI is simply a faster, more hands-off way to find the same low-quality leads you get from DMM, cold calling, and SMS marketing.You’re not improving lead quality—you’re just finding bad leads faster.

The "easy" answer - short term rentals where your brother participates materially in the operations - this would mean 500+ hours a year.It sounds simple from a tax planning perspective. 

I mean, is it as simple as finding a few recent sales within a few miles on zillow or is it as complicated as finding a commercial RE agent who I'd have to pay to give me a CMA?

You can hand them over all your information to organize at tax time and their staff should be able to organize everything and get your taxes filed.

If they can do something as simple as this what else are they cutting corners on?

You can too, without being a wholesaler or an agent.You can walk into a mall to a jewelry store and buy gold, which is simple, but you pay a huge markup.

I am a little older, a little more knowledgeable now, and I’m reading everything I can get my hands on.  

Very communicative, hands on, and thorough with their property management.As some additional context, I own a few rentals in different markets and Michele's team is top notch compared to them.

Does anyone know of a blog I could read or possibly a podcast I could listen to each morning that gives me a simple update on daily market trends?