This is Julie Mehl, a licensed Realtor with John L Scott real estate in Bend, OR... with some answers for the questions you asked.
I recently showed a home on Wagon Master and so I am quite familiar. The area is gorgeous, but this community of homes just south of Sunriver definitely gets more snow than Bend, probably twice as much. The HOA dues are $255 each quarter, but they include: care of a paved street, Clubhouse/Rec Room, Pool, Sewer Assmt, and river access.
This neighborhood is about 5 miles or a 5 to 10 minute drive from the grocery stores, restaurants, shops, and other amenities at Sunriver.
Are you coming to visit Oregon in the near future? I would be glad to show you around. Are you looking for a permanent home or a vacation home?
Here to help,