While it is possible to walk to POR, it is not an advisable journey since you'll need to cross a very busy highway with lots of buses and autos, then walk thru a heavy equipment site thru a wooded area just to get to the roadway that enters the POR parking area. There is no safe walkway between the resorts.
You can take a bus to any park from OKW and then a bus to POR, take a bus or boat from OKW to DD and then a bus or boat to POR. There is no direct transportation between the resorts. If you are just wanting to meet somewhere, I'd suggest just deciding on a park (or DD) and a time and meet each other at the bus stop at the agreed upon time.
Enjoy!