While I would love to personally update you daily on weather and road conditions, I am (finally) of an age where I realize I am unable to be all things to all people and the number of hours in a day is limited.
And, besides, there are people who are paid to do that.  I would be delighted to introduce you:

WEATHER
Here: Troutdale 10 Day Forecast
East:  Cascade Locks 10 Day Forecast
East-er: The Dalles 10 Day Forecast
West:  Hillsboro 10 Day Forecast (yes, I skipped Portland.  If you can get to Hillsboro, you can get to Portland.)
Coast: Lincoln City 10 Day Forecast
South:  Ashland 10 Day Forecast
North: Seattle, WA 10 Day Forecast

Okay, you get the idea and can take it from there.  Please be aware that Oregon is a conglomeration of 111 microclimates, of which 22 are in our immediate vicinity (I made all those numbers up) (sorta), so please don’t beat up the weatherman if what you encounter isn’t exactly as advertised.  This area is more or less impossible to forecast with complete accuracy.

TRIP PLANNING

If you’re heading out to the Gorge to see the falls, please check in at the hotel desks or Chamber.  At this writing, the scenic highway is open with no construction in process, so you have a straight (winding, curvy, beautiful) shot from Troutdale out to the Falls, but we’ll clue you in on the lovely bits you might miss without inside information.

The Larch Mountain gate opened on May 27th, so don’t miss the drive up to Sherrard Viewpoint for that beautiful five mountain view!

TRIP CHECK
Very good site which ODOT keeps updated on a more or less constant basis.  Check here for trip cams and any road closures or obstacles.