And of course the traditional components of check in and check out, guest screening, and optimizing prices (though I find the most mgt companies don't do much there)

Sub optimal yield is better than a capital loss.If you want to learn more about value investing, start with The Intelligent Investor by Ben Graham.

Your potential income with additional costs is your best case, optimal scenario.

Utilise the available resources(contacts, podcasts, meetups etc) to optimize learningAll the best forward

My day job is in A/B testing websites and doing conversion rate optimization to get more revenue/purchases from people visiting websites. 

Continue exploring various strategies to optimize your purchasing power and minimize upfront costs.Using an FHA or VA loan for MFH acquisition can indeed be advantageous, offering lower down payments and favorable terms.

My approach could be sub optimal at which point I can make the required changes.

What do you think would be optimal for both parties?

As for the property itself, I'm thinking that a fourplex with a 3/2 + garage setup would be optimal, as it would attract families who would stay for a long time.

They're the pros, after all, and they can offer tailored advice, ensuring you're not only correcting the mistake but also optimizing your tax situation.Good luck, and definitely consider getting professional advice to navigate this.