I have a good FT job in education administration, but I want to retire asap, focusing on RE (so, not really retiring, but you get the idea).

A few things to consider:Selling and 1031 Exchange: Moving to a 2-family is a great idea.

Great idea from @Henry T. to live in the ADU if you can and rent the house.

As you can guess the three of us have different ideas on what to do.

A good mix of LTR'S is a very good idea so that all your eggs aren't in the STR basket.I like tourist destinations where STR'S are heavily ingrained and almost impossible to ban or regulate out of existence.

All thoughts and ideas are welcome.

It’s a good idea to confirm you have a path to record title in a way that’s financeable, even though this isn’t a standard fee-simple sale.The big question is whether it’s reasonable to pay a market-rate price when you’re not actually scooping up the land.

I’m here to connect with like-minded individuals, exchange ideas, and continue learning from this incredible community.

I'm a fellow real estate investor and I own properties throughout New Hampshire and Maine Southern Coast, I'd love to connect and bounce ideas off each other. 

Besides, it's always a good idea to build a good relationship with the Planning and Building departments.