Hello, I'm looking to build an ADU on a property and then convert the two homes into a Condo association.

Let they sign something that they'll cover all your costs associated with taking any of their advice.

., repairs, maintenance, insurance) associated with a rental property.

In the next 1-5 years you could have some serious cashflow - why would you care about the associated taxes?

I am curious if it is associated with bigger pockets? 

I hear appraisals associated with ADUs regularly in southern Ca and they are typically less than 50% of hands off cost.  

.- The numbers may have an impact on your decision.You may also want to read your condo's Home Owners Association Master Deed & Bylaws to make sure there are no restrictions on any type of rentals. - Many HOAs have LTR restrictions and some now have implemented STR restrictions.Also, hopefully you've updated the home insurance policy of your current STR rental from a homeowner's policy to a landlord policy.

In addition, the capital outlay starts long before any income and the detracting of something from the primary structure even if it is just yard space.As indicated, my original protege made a lot of money (over $500k) on a land transaction associated with a large count ADU development.  

I’ve come across options like the Institute of Real Estate Management (IREM), National Association of Residential Property Managers (NARPM), and Certified Property Manager (CPM) programs, but I’d love to hear opinions on which have been the most valuable in practice.Additionally, any recommendations for resources, books, tools, or online communities that have been helpful for day-to-day management would be appreciated!

Start by checking investor forums, networking groups, and local real estate investment associations for recommendations.