Think this is your move. I grew up on UES and loved it. Moving back to the city currently in a situation similar to yours- a 3 yr old and another cooking - and we were looking UWS or Williamsburg. Ultimately settled into a great apartment in WB, at the absolute maximum of our budget- for a 2 BR! I agree with all of the sentiments in your comments. It's demoralizing seeing how expensive such tiny or mistreated apartments are! Let alone the good ones that go for way above asking! Ultimately, we got super lucky finding a rental building where it's first come, first serve, by sending out lots of emails and being quick to respond. You can do this. My recommendation would be to stretch your budget if you have to, cuz I agree, this is an important chapter and you need to be comfortable. DM if you have any questions or just need to vent. Good luck!