I agree with @Michael Plaks - having them provide financial and tax strategy together is not necessarily a good thing.Interesting to note - all of the largest asset management / financial advisory firms I work with...none of them do tax work, they all coordinate with a tax firm to address those needs.There are true "fee only" financial advisors out there. 

I would basically do what this owner is currently doing, which is more or less property management.

Even in a perfect market with low interest rates and high resale numbers, and the perfect Contractors and Property Managers.....

MANY self-managing landlords violate Florida law and don't even realize it... they just get away with it because the tenants don't know. 

Ask for help from a real estate expert or a company that manages properties to spot great deals.Good luck!

First property has been renovated, leased, and managed in line with all timelines and expectations.

I am curious what expenses others pay through their property management LLC on behalf of their rental properties.  

If the home sales start to increase it would be around late 2025 so by early to mid 2026 that would be your window to refinance and pull out some equity.You would probably see the rental market increase by late 2024 as the initial plant managers and workers move to set up shop. 

(He does some levels of property management and knows everyone).

I've seen property managers charge a % or flat fee to do project management or coordinating multiple vendors for say a make ready repair turn.