Is this going to give him bad sleeping habits? and a few extra ?'s?

You can just start soothing him a bit less. It doesn't have to be all or nothing. Soothe him as you usually would, but leave him a bit awake and drowsy, and put him down so he can start to practice falling asleep. Over time you can soothe him less until you have a routine that you are both comfortable with. Try the book Healthy Sleep Habits, Happy Child. He is a proponent of cry it out, but the important thing to remember is that crying it out is a last resort, not a first line treatment of every sleep issue. Your little guy is still young and just needs some practice. And yes, boys have a way of sleeping on their tummies and wetting everything in sight. You can try: using the next size diaper, adding a diaper liner to hold a little bit more, and putting the diaper on with a little more material in the front. Also make sure that you are pointing his penis down when you diaper him!

You can rock him, shush him, nurse him or sing him to sleep as long as you want. My son is almost two and I will rock him with a warm bottle until he's almost asleep then put him in bed almost asleep. I didn't start that until he was over a year old. I was, and still am, in no rush to force independence on him. I very wisely avoided the whole sleep conversation with my son's doctor with a very vague "Oh he sleeps very well" answer to her questions. I never volunteered how I put him to sleep or how much he woke up. Your son's doctor probably gave that advice to self-soothe because she thought you had issues with how your son sleeps. At 5 months, my son woke up once a night for a bottle. I don't remember how often my son ate at 5 months, but he was getting 6 ounce bottles. No teeth until 10 months. Sat at almost 6 months, rolling over like a pro. Didn't crawl until closer to 7 months. Yes, he likes to sleep on his tummy and it seems like he's always peeing through his diaper when he does. I even make sure his "equipment" is pointing down. It's normal.

Put him in his crib and let him go to sleep on his own. Also, buy a sound machine that plays 'nature sounds'. The nature sounds are calm and soothing which will help with his sleep. As for his sleeping position...................no matter what it is - leave him be because he's comfortable.

5 months is too early to let him cry it out

Personally I think self soothing is important but is something that is learned when given the chance. I was blessed as my daughter started self soothing at a few days old by suckin her fingers and now if she is upset or tired she sucks her fingers and as she gets older I will break her of that but right now it's healthy. For self soothin you can do your regular nightly routine but instead of lettin your child fall asleep in your arms you put them in their crib so they learn to fall asleep alone. You may get some fuss but as long as your child ain't cryin for an hour non stop they are fine. at 5 months old my daughter was sleepin through the night but that's because she knew how to put herself back to sleep. She was drinkin 6oz of milk every 4-5 hours with an exception of at night since she slept from 7pm till 7am. She was teething and had been since 4 months but she is now 9 months and only 1 tooth has barely punctured the skin and another is workin on it but you can't see either tooth only feel the edge of the one and the swell for the other. My daughter learned to crawl and even pull up and walk with support at 5 months but I was told that was highly unusual. And I believe it was due to her spendin all day (cept nap time) on the floor and the fact she was workin with a physical therapist for some muscle problems. As for little boys peein out of their diaper definitely pay attention to which direction you point his penis when puttin his diaper. It should be pointin down not up. Good luck and best wishes!

At this point, it may be a little early to teach him to self soothe. A few minutes of crying wouldn't do any harm, but just leaving him to cry it out will only lead to a child who thinks that he's being abandoned at night and that will lead to issues. If you want, let him cry for a few minutes, then go and soothe him without taking him out of his crib, then leave him. If his crib is in your room, lie in bed so that he can see you, if it's not, sit in a chair in his room so that he can see you. What you're doing isn't giving him bad habits, there's time enough to break them, right now you're teaching him that you love him and will be there for him no matter what. My 5mth old has one tooth and can sit up though he's still a bit wobbly, so I only let him sit without support in his nest. He will sleep from about 9pm till about 4am, when he'll wake for a short feed (I breastfeed), then back to bed until about 7am, followed by another feed, then, if I'm lucky, he'll fall back to sleep again until about 9:30, then he's up for the day, no naps, not even when we take the 40 minute walk to pick his brother up from playgroup. Crawling - no, at this age, they're a little too young! I have two boys and I've never had that problem with them sleeping on their tummies. You do need to manually position them before you tie the nappy because little boys will stand to attention and they will pee in whatever direction that little penis is caught in. My 5mth old still sleeps on his back though, unless your little guy is rolling over onto his tummy by himself, don't lay him to sleep on his tummy at this age.