ETA: LO is 14 weeks/9 weeks adjusted

Sorry in advance for the novel! We've been consulting with an RN/Sleep trainer about all of LO's sleep issues, and are doing what I call, "sleep training LITE", where we let him cry for 5 mins and then go in and soothe him for 1 min by stroking his forehead, putting a hand on his chest, and inserting his paci (I'll reference the cry/soothe cycle as C/S below). When he starts crying again, we re-start the timer, rinse and repeat. We started on Jan 3, so we're on day 16 of this. We've seen significant improvement in his daytime sleep. He previously couldn't sleep longer than 5 - 30 mins in his crib, but now his first 2 naps of the day are almost 2 hours long (I usually have to wake him up from those 2 naps), and he does ONE 3 - 4 hour stretch at night. Naps 3 & 4 are still a crap shoot, but I'll take what I can get.

But bedtime is still a disaster. I can't figure out what time to put him down, because he cries for hours! When we initially started this, we were putting him down around 9 - 9:30. Then brought it to 8:30, then 8PM, then 7:30PM, and last night I tried 6:30 just for shits and giggles. FYI, our bedtime routine is bath, lotion, pjs, white noise, bottle, swaddle, 1 board book, and crib. It can take 60 - 75 mins because he is a slow drinker and that bedtime bottle can take up to an hour. In terms of awake time between last nap and bedtime, it's usually about 90 mins, including 15 - 20 mins of play and then we start his bedtime routine. Here's a recap of the past few days (mainly focusing on bedtime issues, the rest of the night isn't great either, but bedtime is the worst):

Thurs 1/15: 8AM wake up, 4 daytime naps = 5 hrs-ish, in crib at 7:30PM. 3.5 hours with 8 C/S checks, didn't officially settle to sleep til after his bottle at 11:45PM, so almost 4 hours after we put him down.

Fri 1/16: 8AM wake up, 3 daytime naps = 4.5 hrs-ish, in crib at 7:30PM. 8 C/S checks, didn't officially settle to sleep til after his bottle at 11:40PM, so almost 4 hours.

Sat 1/17: 7:50AM wake up, 3 daytime naps = 4 hrs-ish, in crib at 7:44PM, 2 hours with 5 C/S checks, asleep at 9:50PM. This was our best night yet, where he did two 3 hour stretches after settling.

Sun 1/18: 7:25AM wake up, 3 daytime naps = 4 hrs-ish, in crib at 6:30PM, 4.5 hours with 13 C/S checks, didn't officially settle to sleep til after his bottle at 11:30PM.

So last night's 6:30 bedtime resulted in the longest amount of crying. So do I go back to 7:30? I have no idea why he fights sleep so much. Everything I've read said that night time sleep is the easiest to resolve cuz their brains are hard-wired to fall asleep in the evening... apparently not my son. HALP!!