S.B.
That's a lot of change for a five month old. I would just do things gradually. As far as wakings, both of my children woke for feedings one to two times a night until they were a year old. I am not against babies crying it out a bit, but I don't let them get hysterical. And if they were hungry and not fed it started the hysterics. Our pediatrician told me it was fine to continue feeding on demand.
Neither one of my children would take a bottle...ever. I could leave and they would go without, usually screaming themselves to sleep, rather than take a bottle. When my daughter was born I was determined she would take a bottle, unlike her brother. I started earlier and more often. She still refused. It was very frustrating and stressful. But a sippy cup saved us. I bought the gerber soft spout and took the stopper out of it. We just fed them like you would with a cup. The sippy cup makes it a little less messy, but it's still a mess and you have to be careful not to accidentally give them too much. For whatever reason, maybe the novelty of it, my kids both drank from the sippy cup. As an added bonus, they both were able to use a sippy cup unassisted by the end of six months.