Ji Jenn,
the crying before sleep isn't uncommon, sobbing can be a mantra cry---which is infact a selfsettling type thing. I would encourage you to stay with him to help if he is truely upset and crying. The main thing is that you are not leaving him alone to cry-it-out. Tracy was totally against CIO as she felt there was a gentler way and it broke the bonds of trust.
I think first look at a nice windown to get him relaxed and then follow that windown rouitne for all sleep times. ie. close blinds, swaddle, lullaby and in to crib.
If you'd like you can start patt-ssh with him over shoulder until he is nice and relaxed and then move to the crib and continue. You need to find what works for him in terms of varying patt-ssh. the main idea is it helps them calm because they can not focus on 3 things at one time (ie crying, sound and patting) so hopefully they stop crying and instead the sound and patting sends them off to sleep. The swaddling can realy help them feel secure aswell.
In terms of your EASY, you should try to set it up for a 12hr day and 12hr night. Ideally the night sleep should start no later then 6:30/7 with a 6am wake. Also at his age he should be nursing at 3hr or so intervals with 3 naps of 1.5hrs and a catnap of 40min.
so
wake6
bf 6
nap 7:30-9
bf 9
nap 10:30-12
bf 12
nap 1:30-3
bf 3
nap 4:30 for 40min only
bedtime routine, final bf, bath etc 6pm and in crib for 6:30
the only reason I suggest this is it allow for more BF during the day, it also will increase the night sleep and decrease the day sleep a bit, which will make it eeasier for you to get the naps in the crib. Also as they get older and start to drop naps, you really need the night sleep to be at least 11hrs.
I think you should start a nice long winddown about 15min before the goal nap time and aim to have him in crib all drowsy and sleepy if possible. Also, you will eventually have him in his crib more awake as time goes on as the end goal would be independent sleep.