Hi N.!
Well, everyone has a different parenting style. I always tell people "do whatever works for you, and if something stops working - change it!" :) On that note, it sounds like your bedtime routine isn't working for you anymore. I'll share a little of what we did with our girl (who now LOVES her naptime/bedtime...truly!).
We did sleep training with my daughter when she was 5.5-6 months old. We did do some "Crying It Out", but for us, that meant leaving the room and going back in at intervals, lengthening the time between intervals. She took only 2 nights, but was already sleeping through the night for the most part. We did find that she stopped waking altogether once she was putting herself to sleep...I think it helped her figure out how to "roll over and go back to sleep". :) Naps took a little longer, I think a week or two, but we were SUPER consistent with timing of everything for those weeks so we could establish a good pattern.
You can't spoil a baby - they need all the lovin' you can give! But at this point, it sounds like you are wanting things to shift so that your nights belong to you again, and that is OKAY!! My favorite sleep book is "Healthy Sleep Habits, Happy Child" by Weissbluth. For older babies, he usually recommends the extinction method of crying (close the door at bedtime and go back in when the sun comes up). I didn't feel good about that with my daughter, so we went in at intervals, but didn't pick her up. But again, she was younger and fairly immobile, and I know that makes a difference. You may want to try "extinction" for the middle of the night wakings, or at least really limit the number of times you'll go in there. There will probably be some crying, but in my opinion, there are worse things in the world than crying! ;) You know your baby, so listen for changes in the cry, but some of his tears are likely exhaustion...haven't you ever been so tired you cried? I know I have...
Good for you for working on it now. It doesn't get easier as they get older, and sleep is really important for brain development/recovery (for ALL of you!!). Check out that book - it has comments on all ages/stages. :)
Take Care,
R.