Do any investors, legal experts, etc. have any idea how the legalization of ADUs might change the possibilities of owners adding units to existing properties?

Not an expert but I would say MA gets none from the sale out of state.The IRS probably wants their cut of capital gains.

Your thoughts and/or expert opinion would be appreciated.

People need know you, like you and trust you.You need to be able to show you are an expert on the market and the space.

I'm game...A snip-it from a post I did on this thread about investing in Wisconsin: Milwaukee is sitting on some of the most affordable housing in the country, is adjacent to one of the largest freshwater lakes in the world, has entertainment & food that rivals every major metro, it's sports teams bat way above average for a small market which attracts hundreds of thousands if not millions of people here annually, economic development has been happening at a level unprecedented since the '50s (we are breaking ground on the world's largest mass timber building in June), has a tech ecosystem on the ground floor of attracting major talents with partners from the fortune 500 companies in town... 

One of the first things we learned was the difference between physical occupancy and economic occupancy.

You can read all the books you want, listen to all the gurus, watch all the videos of "experts", but until you are knee deep in your own deal, you will never feel what it feels to be an investor.

We are considering self managing once we get enough properties that make it economically feasible and have already bought the software to do so.

Ease up on the agro responses.The reason the code limits losses in a whole number of areas is to not incentivize activities with limited economic substance.

The developer selling the deal, your own numbers, or an impartial 3rd party market expert?