The Dillema still continues!

So I don't know what i am doing, if anyone has any advice on how to transition from 2 naps to 1, that would be most appreciated. Yesterday Jordon acted so tired, he took 3 1/2 hours of napping but wouldn't really go to bed until about 8:15 which isn't bad, but he woke up at1:30, and i am doing the dr. sears method now, so i went in to comfort and to help him go back to sleep mostly, but after 15 minutes of it, i was able to leave him without him noticing even though he wasn't asleep yet, he eventually went back to sleep, but woke up at 5:30 ready to go for the day after only sleeping barely 8 hours for the night. He went down great this morning and slept almost 2 hours before we went to our dentist appointment. But when it came to a second nap, he refused at 1:30, 2, and 3:15 i gave up completely and decided to put him to bed early. He was falling asleep at his dinner around 5 and since he almost bit off his soft sippy cup spout, i just gave him a bottle tonight, and yes he fell asleep on the bottle, which i hate when that happens. So please cross your fingers for us that he sleeps all the way through until at least 5 in the morning to give him a good 11 1/2 hours of sleep. I'm getting kindof exhausted here. It's just very frustrating, because i think i'm pushing him into 1 nap a day too early cause a lot of those days he does cuddle on the floor quite a bit acting tired and ready for sleep, but when he naps he either naps great or only wants to do a morning nap and won't do the afternoon one. But then when i give him great naps in the day, he doesn't sleep good at night, it's like he needs to be completely worn out in order to sleep well! So that is my dillema for the week. I think tomorrow i'm going to do 1 nap, see if he wakes up at 5 and see if i can push his nap time until 10:30-12:30/1. Wish us luck, and please don't hesitate to give any advice. I look up tons of stuff online but family advice is always much better. Thanks for all your support!