If out of state, it'd be a combination of someone else (maybe an assistant) and I'd manage paperwork, leasing, as much as I could from here.

This combined with minimum footage for a bedroom means many lofts do not quality in CA as a bedroomDifferent states will have different requirements for what constitutes a bedroom.  

It sounds like you’re setting up for a solid multifam portfolio—between you and your dad, the combined entitlements give you a lot of flexibility.

Then combine with ADU.  

With the current interest rates vs the extremely low rates we had for the last decade, combined with higher house prices, cash flow is going to be less than it was 5 years ago. 

The other reason tax bills get stalled in Congress is that most bills combine multiple unrelated measures, usually serving various special interests.

We are excited, at times frustrated, and have a healthy level of anxiety, but all of those elements were expected from the start.I'll try to keep this thread updated, as it has always been helpful for me to read others' experiences.

Imo, this is the critical element.

That said, the right team on your side can make the permitting process and inspections far less painful.I’m curious... as you refine your plans, how do you see yourself balancing the home’s original character with these modern upgrades, and which element of the design do you think will win over the pickiest buyers? 

Sounds like their combined income likely beats your other tenants.Your gut is probably your best bet and you need to go with it.