He clearly knows the best course of action in this challenging market.

Challenges?

The refinance stage can also be a challenge since many lenders require a seasoning period, often around 6 months, before they’ll allow a refinance based on the new appraised value.

After contract is more challenging as your best negotiation is before contract.

While I agree the rent by the room strategy can be great if you know how to manage it well, from a lending perspective, a lot of 30 year DSCR note buyers won't allow properties with individual room leases, so it could make refinancing more challenging. 

Challenges?

I wonder if rent control laws will be easing anytime soon in this city - other than capping rent prices, I don't think they do anything to help improve the quality of rentals.

This is just the latest case study of how Government is incapable of improving housing affordability on its own.

Without solid credit, even the best structure can be challenging to leverage.Curious to hear how others in this community are structuring their businesses—are you sticking with an LLC, making the jump to an S-Corp, or considering something else entirely?

Challenges like this can ultimately set the stage for a better-performing asset in the long run.