If the SEC came sniffing around and your main job was raising money and all you do is attend a weekly meeting, good luck to you! 

Any insight or information appreciated, thank you!

I’d love to hear from anyone who has done this before, how did you structure it, and what worked best for both parties?

Start by analyzing cash flow and market demand for each property to decide which one to rent out.

They probably want to be certain YOU are legit.Most of the scams I've seen are by non-owners. 

With enough knowledge you can make a educated decision on which approach you take.My experience:I personally don't sign up for any program who take you aside during events and try to sell packages that is just blatant sales strategy.Once you sign up there is every attempt to make you sign for their programs for bookkeeping, registered agent, LLC or corp setup fee which have ridiculous even with platinum membership.Basic standard structure they suggest to take advantage of multiple deductions can be easily achieved by proper education or work with a good firm like https://wcginc.com  who is local to you.A umbrella C-crop to manage all other LLC properties and take advantage of many tax deductions that are not available with a llc, its also used to take losses up to 100K as startup expenses and dissolve the entity after few years.Few LLC entities for investing in Real Estate, etc preferably in Wyoming or Nevada ( you can find many companies online who can do this for $150 compared to anderson $1500-$3000) , they will claim they have a secret Operating agreement which is bogus.They certainly try to take advantage of tax loopholes and claim to be smart people, my view they are just taking advantage of numbers as per their own statements.

When you say you want to prioritize cash flow over equity, you want to watch out for people honing in on that and selling you "good cash flow" deals which will be in D neighborhoods and will come with high capital expenditures and harder tenancies.

How can we know which boomer is going to list their home?

Thank you in advance!  

Thank you!