OKW is a great resort. My grandparents bought back in the early days when it was the only DVC resort so I stayed there a few times I my teens, and we have stayed there 2x since becoming DVC owners in 2012 (AKV is our home resort). I really like the Conch Flats theme, Olivia's is a solid restaurant, the main pool has a very deep end that I can cannonball in with my kids and not slam into the bottom of the pool, Turtle Pond pool is nice if you want a quieter experience away from the crowds, the Community Hall is great for families (we spent several rainy nights there playing games and doing other activities w/ our kids), it's fairly conveniently located to all parks via vehicular transportation, has good dedicated bus service, and boat access to Disney Springs is also nice (it was especially great during the construction during the transition from Downtown Disney to Springs).
It is the oldest resort but IMO has been well kept, and we haven't even stayed in a renovated room yet. We may have the chance next year because my parents are coming with us and my mom wants to stay at OKW, I think due to sentimental value and both of my grandparents (her parents) having passed on and the memories of our trips there as a family in the 90's.