This is a very difficult situation and there are no perfect answers. In light of this, I will give you some suggestions.
First, at 8 months old, a baby can be sleep trained. So, this might be a good step in the right direction. To do this, you will need a routine, so that the baby will get to know that it is sleep time. This will require you to be consistent. This is the most important point. Consistency is a perhaps the best teacher for babies.
Second, along with sleep training, you will need to create a consistent daily route as well. This will allow Bobby to form good habits. So, eating should be done at the same time as well as other activities.
Finally, if Bobby is active, then it might be good to baby proof a playroom where Bobby can explore and be active. This will also tire him out, which will help with feeding time and sleeping time.