My first gun was also an 870 Wingmaster. I used this gun for almost 30 years although I bought many others. I always ended up with the old Wingmaster when I found myself questioning my shooting with any of the newer guns. When my kids came along, I didn't hunt much so the 870 worked out fine for the few occasions I went out.
A few years ago I hooked up with Ol' Dan and got back into serious waterfowl hunting. I was lent a Ithaca/SKB XL900 auto from my buddy Tom and I shot it well, I really liked the feel of the gun and found I felt less recoil. I decided to look for an auto. I ended up with a Browning auto-5 mag that a guy at work was selling from his fathers estate. This gun fits me well and I've probably shot more birds with this gun than in all the years I used the 870 combined. I also bought an SKB autoloader (same as the Ithaca, which SKB made) and I use it for upland and the occasional duck hunt. I doubt I'll shoot the 870 much anymore other than to revive the memories of hunting with dad and past hunts.
For me, the auto is my #1 gun.
Dan