Our intent was to sell, but we are not having luck and need to move in another direction, carrying costs are draining us. 

Make him carry the insurance.

This MIGHT put us back in budget - but I'm not convinced it doesn't also carry significant risk at this point.As a side note, because of how much cash any of these solutions appears like it will take us, we're wondering if there are personal lenders or hard money lenders that do these deals. 

After posting a monthly market update for Milwaukee every month for the last 5 years and looking at the data every month and the dynamic that makes prices inch up month after month it is becoming more of a certainty to me than a possibility.Because the reasons don't change: we keep devaluating the paper dollar, we still have a chronic housing shortage and we are not building nearly enough to even keep up, let alone to catch up from the deficit we carry.

Realtors generally carry E&O insurance which would be the first thing I'd go after. 

Shiloh Lundahl -  Man this is gold. 

Milwaukee is very often misunderstood; what looks great online and on paper (super low price, high cash flow) is usually fools gold in the form of a 100 year old hours that needs everything new, the poorest neighborhood, and high maintenance tenants.

Of course there is the rabbit hole of owner carry options too, but the above is the most straight forward option. 

That person has negotiated a cut of fees and carry with the main GP that actually operates the deal.  

If you plan to live solely off rent I don't think you can carry a total debt load greater than 25-40% of your total portfolio value.