I have only done residential in the last 12 years, but have done a couple of deals with partners in my office for commercial and I can tell you, that commercial has a lot more math, less emotional and more detached than residential. 

The bigger upside is that if you decide this is not for you, they're much easier to sell.Your biggest obstacle is going to be financing.

I can't see growing ever really working in an apartment setting, but SFRs with an outbuilding (detached garage, etc) might be workable.

On my first property I considered converting the detached garage and/or the basement to an ADU.

Detached Structures: for other buildings on the property (ie. sheds & detached garages)Again, there is normally an included limit of 10% of the building limit.

very excited about this law change. opens up the possibilities. more way to manuever the government obstacles. 

Also convert the detached car garage into an ADU.

Let’s say conservatively it’s worth about 700k.2.We would be looking at building a detached rear unit with res over a 2 car garage + storage. 2 beds 1 bathroom.

What obstacles and opportunities have you encountered with it?

I am in discussions with another architect to partner on design and finance of new semi-detached development in the east york area.