Yes, I would make sure that we did not go past the next feed, so if feed was at 3 and we had a good nap, I would make sure my lo was awake by 6 for next feed. If it took lo a long time to fall asleep, I would not let her go pas the 4 hour mark.
What I did with my DD while she was young, I used to pat / shhh her and just hold the dummy in her mouth until she was alseep. It was not the best scenario, but it did help her get to sleep quicker.
When we had the fussy days where she did not sleep well I would do a little APOP (accidental parenting on purpose) cause with my DD breaking habits was far easier than trying to get rid of the OT monster.
We especially had problems when it came to the cat nap. I used to lay with my DD on our bed and cuddle her for the cat nap, that way I was sure that she would get her nap and not be OT for bedtime. THis did not pose any problems for us, as we still made sure that we did all our ther naps int he cot/moses basket.