Would you personally intentionally go out and do this?  

Non-passive to achieve this level of return.Add the addition of the ADU makes the main unit rent controlled if over 15 years old.the work to add an ADU likely exceeds the effort of a brrrr that can achieve infinite return  Experienced investors are adding multiple ADUs by leveraging items like bonus density, committing units to affordable housing, etc.  

We have our main monthly meeting on the 2nd Tuesday.

The intention is good and there can be some solid advice. 

But when we are done it’s going to look sleek and intentional.

It has to be an addition.I would double check because maybe the workaround is reinforcing the garage and building above it.We lived in our studio ADU for two years before we moved into the main house.Best thing to do is talk to an experienced lender.

Main problem is that I wouldn't be able to get out there after every visit to clean and check up.

What are the main reasons condos are considered vastly inferior?

But from what I have seen it has a lot of useful accounting tools that should make my life significantly easier, and ultimately that's what my intent is.

The main risks I would say to watch out for are any family dynamic issues that could arise as things like this could lead to issues that didn't exist previously.