I'm forced to wake my LO from naps SO often and I hate it.
His naps are totally all over the place and I never know how long he will nap for, could be 40 mins or it could be almost 3 hrs!! I did consider trying to sleep train to extend his naps to a more regular pattern but tbh the number of times I have to wake him to take him out (it's impossible to lift him and not wake him) there's just no point in my trying to make it regular, I'd only have to disturb him again. I wish I could just let him sleep.
I almost never wake him if we are staying at home although there has been once or twice, like you I have done to keep BT on track. The other night though he'd missed his afternoon nap from being out, was massively OT, then couldn't settle for a nap because he was so distressed and OT, by the time he was asleep it was 5.30pm and he didn't wake up so must have gone into his night time sleep and just decided to skip his bath/feed/bed routine. I eventually woke him at 9pm and kept him up until 10.30pm. In that time we had quiet cuddles, watched some kids TV I had recorded, a feed, a wash and into pjs etc. He always has a feed at 10.30pm which I class as a DF but have to wake him for, he is so used to this that he stirs at this time anyway and always falls immediately to sleep after it. It's the only time I don't feel bad waking him because I know he wants a full bottle and can't get through the night without it.