J.H.
Well, I can tell you, we did the cry it out method. This is HARD as a parent. Luckily our son wasn't TOO stubborn. He actually did well in the crib on his own for the first year. Then it turned into him getting up in the middle of the night and ending up in bed with us. This lasted about 3 months before we couldn't take it anymore. I called my mom, and she of course gave me the advice of let him cry, as did the doctor. The first night was absolutely horrible on me as a parent. It took about an hour for him to stop crying. I first put him back down in bed, rubbed his back for a few minutes, then sat in the middle of the room. About 20 minutes later, I moved next to the door. Yes, he was crying during that time and yes, it really took a toll on me. After about an hour, he finally cried himself to sleep. Any longer than that and I would have lost my mind. The next night was easier, probably only about 45 minutes. By the fifth night, he realized I wasn't picking him up. I just came in, put him down, rubbed his back and left the room. He cried for less than a minute. It has been fine ever since then and he is 4 1/2 now. Knock on wood, I don't run into the problem again. On a different note, my friend had the same problem with her son. Her way of handling it was to just let him stay up until he crashes. Then they move him to bed. For her, it works, but he has no set bedtime and doesn't crash till 11 pm or later. I don't think it's healthy for him, and also I like my unwinding time at night. All day long till 9 pm, I'm working or I'm mommy. I'm thankful for my peace at night. And although that first week was incredibly hard, it really did work. That's the only suggestion I can give you. Hopefully you can do it and it will work. But not all moms can let there baby just cry. It's hard. Maybe get some headphones. Just kidding, but seriously, it's hard on the mama heart. Best of luck to you.
Oh, and btw, your son shares his birthday with my sister. Pretty cool.