I'm considering partnering with a non-profit that would manage the sober-living program; with me just providing the house passively for rent on a per bed basis. 

Depending on the location and properties, consider having a game room.

@Ryan Cousins it's really going to depend on YOUR analysis/projections of what you think the property will be worth in the future.You'll want to compare that to any capital gains tax-savings if you sell now.

Therefore, you would need to file partnership returns for each LLC.Given these considerations, both approaches could be correct, depending on the specific circumstances of your LLCs and state laws.

These involve additional costs.I am not saying that there definitely is negative cash flow, but I will say not including known expenses is providing a misleading cash flow estimate.  

It can depend on the property, but owner paying the bills seems rare these days. 

Sharing your goals can help others provide more specific advice! 

And, depending on where your properties are in Portland, the value might be near its peak—selling while they’re in top condition could be a smart move.Ultimately, it comes down to what will give you the most peace of mind and the most flexibility for the future.

I see that real estate agents and brokers are too negative on sub to deals……investors looking for low interest rates and or low down payments are too positive on the same.As I stated the reality is somewhere in between, depending on individual circumstances.  

Hoping that someone could provide some guidance on this so I can decide how to proceed?