There are likely larger users out than than what I deal with, but at that SF at least in my world you are likely looking at multiple tenants, not sure if thats what you planned or not.additionally something else to consider is the cost of buildout on a med office space. depending if they are going to have x ray or not its not uncommon to see $500-$800K buildouts in my experience. 

Structural engineer is definitely first step as Mason mentioned.It totally depends on liquidity, risk tolerance and time.

I think it would, depending on the celebrity of course. 

Depends on if you are hiring a builder to build or if you are the builder yourself. 

@Brian KohtzYes, you can potentially claim the property as a rental in 2024, but it depends on when it was "placed in service" for rental purposes. 

From what I understand it’s neighborhood dependent up there.

That said, the other agent and I frequently reduce our commissions on these deals to make them work and, even if the agents don't, the seller would still be getting around 3% at closing with a 10% down payment which, to me, could be a win-win depending on their situation.  

It might even work if you don't house hack, just depends on how much rehab is needed.

Getting a lower rate will also depend on the amount you're putting down.

You could make this work ST, MT or LT, depending on how you approach it - the key with unique grounds is owner-provided upkeep and service built into the listing and what permits allow.