Well, I don't have any advice really on how to get him from drinking out if his bottle, we just gradually took it away, but he also had cousins and daycare kids that drank from a cup, so I think that helped. With him drinking water, we did have that problem, even if you have to put it in his bottle, he's only 10 months, it's fine, my son was over a year before he got off the bottle, put a teaspoon of sugar in his bottle of water, it helps with the taste (also cure hiccups), with the constipation, add some Kayro syrup to his bottle, it can be in milk, juice, or water (we had to do that for our son's constipation). But he will make the change from the bottle to a sippy cup eventually, he sounds pretty set on his bottle, so you might not be able to get him to switch, I truly think he will switch when he's ready.
Also, have you tried letting him pick out a cup from the store, that also worked withour son. Anyway, I hope he makes the switch, but truthfully, he's still a baby, now if you're having this problem and he's almost two, then it's time for some tough love drinking! ;-)