Well, I'm like you and dont like to sleep by myself, but after having my daughter, it seems like the only time I have to myself is when im sleeping LoL. Several months back when my husband and I were having problems I spent a week at my moms house which is about 3 hours away from home, During that time my daughter wouldnt sleep in her play pen so she slept with my in my sisters bed, Needless to say that she loved it.. Something about them being right there next to you gives them great comfort and security, so it was extremely hard to get her to sleep back in her crib when everything was worked out and we came back home. What I did was I'd rock her to sleep (If you shorten her nap by just a half an hour or so, depending on how long their naps are, they'll fall asleep with no problems, at least mine does) and put her in her crib, if she'd wake up when I put her down I'd try patting her bottom or rubbing her tummy to get her back to sleep, if that didnt work I'd rock her a little more, and try again, If that doesnt work again, then lay down with her in the bed, I'd sleep for an hour or so, wake up and put her in her crib, she's usually knocked out pretty good afted an hour of sleeping and goes down with no problems, if she wakes up, pat her or rub her tummy, if that still doesnt work, lay her down again in the bed til shes asleep again, then put her back in her bed. Its a pain in the rear, but worth the effort and a little bit of a sleepless nite, after a couple days of this she re-learned that she had to sleep in her crib, that you would still be there in the morning and such. The way that I have my bed and crib set up (We currently have a big 1 bedroom), is that her crib runs the same way as my bed so all I have to do is lift my head up to see her, She sometimes wakes up and stands up in her crib, checks to see if we're still there and goes back to sleep. We still get a little bit of sleepy time together, my husband wakes up at 5 for work, so at 5:30 like clockwork she wakes up and says "Momma hello" I take her out of her crib and we sleep for another 2 hours together. As for the bottle, water down it little by little till its eventually water, put the regular formula in the sippy cup, if its one with a rubberish valve, take it off till she has the idea down, eventually she'll learn the good stuff is in the cup. as for messiness, every sippy will eventually leak, i dont give her juice or milk unless its meal time, but i always have a water one out and within her reach, she drinks enough to satisfy her and puts it back, i dont let her have it hanging in her mouth like some parents do, because in my opinion its just as bad as the bottle and just as hard on their teeth. the built in straw sippers, take n toss sippers and playtex seem to be her favorites. hope i helped.