Extend Primary Residence w/ Second Story Adjoining ADU (or) Purchase Investment Prop

[Scott Williams]

I am 60 YO. Living in the East Bay of NorCal. I have paid of the house. I am considering as my first real-estate investment to increase the size off the back of my 1st floor primary residential property ~750SF and add a ~750 SF 2nd story adjoining ADU above and convert my ~400 SF detached garage into a ADU studio. The plan would be to within the next 3-5 years move and turn the entire main house, adjoining 2nd story and detached ADU into a rental property for my retirement years. Does anybody have any experience, insight and advice with doing this type of House Hacking? Or would it be better to find an second investment property?