I don't think the big house needs to be there at all!
In the SF world, going from RH-1 to RH-1S is is a much easier change than RH-1 to RM-3.
Subdividing an existing lot further can get into difficulty in some areas with minimum parcel sizes. For example, in Chicago https://secondcityzoning.org/zones/ you can't have a parcel smaller than 1,650 sq ft.
Switching from owner occupied property to something that is a commercial apartment structure can also impact the financial security of a household (you can't evict me from the house I own vs falling behind on rent because of a layoff).
We do need higher density and less impacting houses - but this isn't a simple "tear down the house and build four smaller one" changes for most urban and suburban places.
That's fine. I recognize that legislation has been adjusted by numerous forces to make this as hard as possible. It's still what I want, as long as it's safe to live in places like this.
Suburbia is killing us and wasting so very much for all of us.
These are often called "accessory dwelling unit" and have the corresponding building codes with them.
In SF, I recall them being called "in-law apartments". https://www.realtor.com/realestateandhomes-search/San-Franci... has one that shows a floorpan - https://ap.rdcpix.com/156e0ebabbe946219e56040ab8c44c4fl-m409...
You'll note the two bedrooms and a living/dining/kitchen area on the lower level while the main home is on the second and third level.
Madison, WI recently had changes to make them more feasible ( https://www.cityofmadison.com/news/mayor-and-alders-propose-... and https://www.cityofmadison.com/development-services-center/1-... )
And regarding your space looking at 500 sq ft and 1000 sq ft with the Madison zoning:
So yes, that is the approximate size limit of an ADU.