We have arrived. I don't know if it was turning 2, getting a little brother, my encouragement, or a combination of the three, but my older son is playing some by himself now, thank goodness.
I think more than anything he was just ready developmentally.
So, I want to encourage all of you that are struggling with getting your kids to play by themselves, the time will come. I promise. There are things you can do to encourage it, but when they're ready, they're ready.
Note To Self: It would not hurt to put your baby down occasionally and encourage him to play on his own. (This comes from someone with experience, I don't think I put my first little one down for more that 10 minutes at a time unless he was sleeping and even then I held him a good bit. I swore I would not make those mistakes with this one, but how can you NOT hold that tiny, sweet, adoring bundle of goodness???? But I know I'll be paying for it in a year or so.)