Umbrella Insurance: Adds protection for high-cost liability claims but doesn’t fully separate assets as LLCs do.RecommendationConsider one LLC per city for balanced liability protection and simpler management, paired with umbrella insurance for added coverage.

It does not matter whether you are starting a real estate business, restaurant, car wash, or amazon commerce business - the lender will first look at you and your partner and how much skin you have in the game, your experience and the risk of the loan not getting paid. 

Agree with @Chris Seveney- people LOVE making their ownership structures so complicated when you can mitigate risk in so many simpler ways. 

Sounds like you put in a Bonafide game player but no worries, they suck at the game.

Potential Equity is not skin in the game. 

Felt like being at a high-stakes poker game, but with properties on the line.

Having a PMS with automated reminders has been a game-changer for us too, making it easy to manage renewals without much manual follow-up.

Vacation rentals are a cash flow game really.

Good luck with that one—I doubt any syndicators would find a sympathetic jury in such a case.Scott, you and I have debated the concept of “skin in the game” for years.

Playing the long game, it's not for those chasing rainbows, definently for the LT planned methodical focus.