If you have extra money that you haven't earmarked for additional RE I would do TSM index funds for a truly passive investment. 

So, I would work to increase your knowledge and experience and really identify a strategy that suits you before moving forward with anything. 2.

i've had good experiences with The One Brokerage although they can't do 80% in every situation.happy to keep brainstorming if i am missing something

My biggest concern is managing additional units and tenants.

Had a somewhat disappointing experience with a guru* and now I want to focus on learning commercial and multi-family without wasting money on coaches/gurus.

You may be able to see if a retailer still sells the 2024 version.If you can't get the one time purchase, you would need to see if the cost is beneficial.For real estate -  Quickbooks desktop > Quickbooks online because you can set up multiple entities within quickbooks desktop and not pay an additional cost per entity that Quickbooks online would charge you.Best of luck! 

Do anyone have any  experience of automated tools like CRM integration, Automated lead generation and mass outreach, customer management and appointment booking etc.

Proven Track Record – Experience in vacation rentals matters.

@Travis Timmons thank your for sharing these details in your personal experience.

I recently completed one on a multifamily property and found it to be a cost-effective approach.That said, there are a couple of additional factors to consider beyond the code differences between a garage conversion and new construction:Coastal Overlay Zones – If your property is in a coastal overlay, building a ground-up ADU may require Coastal Commission review, which can add time and complexity to the process.