You have a number of attractions that are accessible from the Bend area:
Lava Caves (there are several in the area), Newberry, Paulina Peak, Sisters, and Crescent Lake, Odell Lake and several other lakes that are along the Cascade Loop SW of Bend. I'm wondering if "Pine, Oregon" is actually La Pine, which is just south of Bend near Newberry Crater. There may be several other places listed that I've missed that could be lumped into the "Greater Bend Vacation Spot" Whenever we head to the OR coast, we try to spend several days to a week in Bend.
Heading south from Bend you'll get to Crater Lake. Nearby Diamond Lake is a place where some here like to camp to visit Crater Lake. Theilsen View CG is one of the CG's on Diamond Lake.
Timberline Lodge is on Mt. Hood.
As for the coastal attractions, you almost need to break it up into north, central, and southern coastal attractions. I'd say see the whole coast, but as you can see from the list, there are weeks of things to keep you busy along the coast. When we went to the OR coast a couple of years ago, we spend something like 16 days on the southern half of the OR coast and still felt rushed.