Which you wouldn't think would be a problem, yet here I am again.

My almost 1-year old loves to nap. He had always and consistently taken long naps. Has also never slept through the night. Currently wakes up 2-3 times. He nurses or takes a bottle and goes right back down.

So, naps. He will typically take a nap two hours after waking up for the day (usually he's up around 6-6:30). He will generally sleep at least two hours. I've been sometimes waking him after 1.5-2 but I feel awful because he seems so cozy. He goes for his second nap about 3.5 hours later and again, I wake him after two hours asleep.
I think this is where we've been running into issues- he needs 4 hours between waking up from his afternoon nap and going to bed a time night- so he's bee having some trouble falling asleep at night lately which is unlike him.
When I do one nap (like if we are out and about) he goes down completely exhausted at 11:30 and sleeps for three hours. The problem with doing this every day is that sometimes he's clearly way too tired to go that long.

What kind of a schedule should I try? How long do I let him sleep? He's so cute, it breaks my heart to wake him up from every single nap.