How do you Mommies use pain medicine when your baby is teething?

My son is 8 months old. His first two teeth seemed to come in quickly and not be that big of a deal. Now his top two teeth have been poking through for a couple of weeks. There are times he seems more bothered by it but he always has whiny moods so I don't know for sure that is the cause. There were actually a couple days he was bleeding. I give Tylenol some nights when he seems uncomfortable but it doesn't seem right to give it every night for weeks. I'm not super conservative with medicine and want to use it if it will help him but I also don't want to overdo it. He seems to sleep better when we give him Tylenol but he's not an awesome sleeper so I don't know if I can blame teething pain for his poor sleep other nights.