I completely understand that "not showing any tired signs" thing! It can be so hard to tell then! That's really exciting about the one long nap though....we're still working to get there. It was looking pretty promising, and then a lot of medical needs came up with DS, so we've been battling making sure we have naps in before having to be at the Dr's office for a while or at the hospital for a while for tests! With all of this, he's added in EW's (5:15 this morning) into the mix so 2 naps are still very common around here! (or at least the trying for 2 naps!).
I'm not sure how long ppl do WIWO...when we were sleep training(at 6 months) we used to rush in everytime DS would make a noise because we didn't want him to wake fully! So aroudn that time we probably did it for about a month. BUT I would be interested to know how quickly are you going in during WIWO? Now you know that he can put himself to sleep, he's just either PO'ed that you walked out or OT. Maybe you can gradually keep increasing the time that you are out of the room. If WIWO is only taking 10 minutes, then maybe you can see if even though he might scream for a minute or two in pure madness, if he would calm himself down on his own and then lay down and fall asleep.
Does he have a lovey, soft music, or white noise? We give DS a lovey (his stuffed horse), he has a CD that plays the same songs for naps and bedtime and we have a humidifier on as some soft white noise. Some nights he talks in his crib for about 15 minutes (it used to drive me nuts...) but a good mentor told me that she looks at that as if they are telling their stuffed animals all about their day!
You're doing great though! Once we can get back to attempting the 2-1 switch, I might need some great encouraging words from you!