Here's what I got going on so farCreated my Company "Coastal Sunrises" which focuses on STR Management/co-hosting, and am in the building process right now for my systems and I'm essentially looking to build every one of them to scale with so I am okay with taking a hit to profits immediately if that means paying employees/va's while I'm not managing a ton of properties.

By making equity raise small and max leverage they try to pump returns with tax savings because the cash distribution is so poor so tout overall returns ( think of Wal-mart touting overall pay for employees at 30 an hour when most of that is covering some insurance and other benefits type fluff versus what someone would take home on a check).

But as an agent, you are a contract employee so if you are trying to buy properties and can't show consistent income, you will only push your dreams further down the line. 

Push out Articles, employee handbooks, brokerage rules.

Investors: should I partner with someone, harnessing their experience (and net worth/liquidity)?

A lot of the STR management companies have contracts with companies to house their employees when they travel for extended periods of time.

I actually do a lot of relocation business with Lockheed and have helped with a lot of employees transferring in and out of Orlando.Best of luck!

Maybe new employees will live in the island 

And ideally, I am perfectly ok with managing the properties on the side of my w-2 job with my brother, but my goal is to get enough cash flow for myself and my brother to be self employed, and hire property management and any needed employees to reduce our workload as quickly as possible, so we can continue to expand into other investments.

Are you an employee being paid a salary to manage the 150 units?