My son's last nap of the day 4:30-6:30 is usually his best nap and sometimes it is 2.5 hrs long but then he is a bit of a bear to try and get to bed for the night. I have always been against waking him because his first two naps are so short and he has to have his soother put in a couple times because of all the noise outside that wakes him. But my question is would you wake him at 6 in order to get him to bed at a decent time (7:30-8)? I wouldn't be able to feed him right away because his last bottle was at 3 and he wouldn't be ready for another until around 7.