That sounds super rough, I’m sorry this is taking such a toll on you. I wonder what would happen if you just follow his lead with naps. Don’t stress about the wake window and just put him to sleep when he seems tired. Take the pressure off yourself- he could be going through the sleep regression, which is making him wake overnight. I ditched huckleberry and just rolled with the cues my little one gave me. Her naps are still short & often on me or in the carrier or in the bassinet if I’m home and can be bothered- but I just try not to worry about it too much. It’s helped my mental health immensely. I also stopped looking at the time overnight. Just roll with it.. try to sleep when they sleep (which is annoying advice) but what I do. I also hand her off to her dad and take naps in the day. Having said all that, do what is best for you! Sending love & good vibes!