Just off I84 between Baker City and North Powder, Haines Steak House. New York Ritchies in Island City, adjoins LaGrande, does a nice job, about 2mi off the fwy. If you want a good burger, Boardman is a bit west of Hermiston, C&D Drive-In, soft ice-cream too and good seasoned curly fries.
As far as the road, I'd check the bad spots here.
https://tripcheck.com/Pages/RCMap.asp It's been good of late, but we have a weather change due mid week. I84 gets shut down in that area with weather enough that checking is a good idea.
Here are the 3 spots to check/watch out for in OR, but they cover about 75% of your OR trip. There are some sweeping curves with moderate hills, Ontario to Baker City, if it's slick, be careful. Then Ladd Canyon between North Powder and LaGrande, a short but potentially nasty pass, can be real bad, especially windy for some reason. I have seen it shut down for wind as well as ice/snow. Then LaGrande to Pendelton is potentially the longest/worst stretch, which includes Cabbage Hill just outside Pendelton.