I am expected to let him cry himself to sleep which i find sometimes work, but most of the time it doens't. I am sometimes pressured to leave him crying for over half an hour and it really hurts me to see and hear him crying so much.
Why are you expected and pressured to let him cry? This can be stressful not only for him but also yourself. Why is he crying (wind/reflux/tired etc). Babies are only little for such a short time, my advice would be if you feel the need to pick him up and cuddle him then do it. You won't spoil him by giving him cuddles. I remember when DD was little we would cuddle her to sleep some nights and when she drifted off we would pop her in her cot. It was a great bonding time for us too. The time will pass so quickly and before you know it they will be too big to cuddle to sleep. The MCHN told me to put her in the cot while she was awake so she would learn to go off on her own but we really only did this when she was happy. Sometimes we stroked her face down her nose which made her close her eyes and she was relaxed and drifted off. This works for DS too although he is a pretty good sleeper at the moment. DD is now 3 and has her nights when she doesn't want to go to sleep but she does after about 10 minutes and the best nights are the rare occassions when we hop into bed for a cuddle with her as she drifts off.