My daughter took to the Nuby Sippy Cups. I got rid of all the bottles in the house. So she had to take the sippy cup. Then she started to bite the Nuby and it started to leak everywhere. She had no problems going to the harder lids on sippy cups.
I started first thing one morning. I tossed out all the bottles and gave her a sippy cup. Yes she gave me that look of what is this thing mom?? But after she was thirsty she took to it. Just don't give in! My mom did it once to me while she was watching her and sent her home with a bottle. It hit the trash can ASAP!
I also think Gerber has a few sippy cups with soft tips that my daughter liked also.
With the bottle to bed thing I can relate My daughter likes the binky. It is tough but she has a special soft blanket and a teddy bear that she is trying to sleep with. Yes she cries in the middle of the night for her binky but I just go into her room and comfort her by rubbing her back. I don't pick her up. I learned that lesson she does not like it when I put her back into her bed. A few sleepless nights is worth getting your child on a sippy just like mine with the binky. This type of change with a small child seems so hard on them but with in a day or so, they dont even realize that it was that big of a change. Us as parents can make things so much bigger than they really are at times.
Well Good Luck (And during this time nap when she naps)