What if you were to offer to pay his monthly net. So basically you are offering to take over the management of the property.
For instance there are several 4 plexes in an area of Portland I am interested in. They are all rented lower than the average rent in the area. 950 per month per unit and avg. Is 1200.
So assuming the gross rent is $3800 and expenses are $1400. I could offer to take the hassle of management and pay him his net every month.
I will assume that the property is rented. Now because gross rent is low, I can increase it incrementally over a 5 year period to create a positive cash flow. If you increase rents 5% each year over 5 years, you will be getting $1200 per unit.
During that time, I could try and offer up cash for 30 cents on the dollar to buy down the principal. For example: in November offer 10k in cash for 30k in principal. This cash would be generated from profits from flips and wholesale deals.
Or ask for a note for 400k at 4.5% over 40 years with a 15 year balloon. $1798 per month.
Please don't hack me on this. Just an concept.