Most babies go through many alterations in their sleep habits and patterns in the first couple of years. What works one month may not work two months later. A baby who actually sleeps a lot during his first two months may suddenly not be able to sleep at three months. Babies who were terrible sleepers for 18 months are able to sleep easily at 19 months. And so forth.
The term 'sleep training' seems wildly misleading to me – invented by someone to sell books to desperate parents. All of us, adult and baby, sleep when we can and don't sleep when we can't. Babies often seem to respond to 'sleep training,' but I'm convinced they were very close to being able to sleep anyway. Some babies just can't and don't (maybe they didn't read those books), and the parents of those babies then feel like they've somehow failed.
My grandson was a very problematic sleeper for his first 2.5 years, and no matter what strategies his parents tried, that was the simple reality of it. And they tried everything, read every book, established terrific evening rituals, tried CIO, and so forth. But with no further change in strategy, he finally just started sleeping better, and now at 5.5, he's still doing great.
Up until he was around a year, we did take turns rocking him to sleep every night. Eventually, he didn't fit in our laps very well, and seemed to have no trouble giving up the rocking. I just don't think it was as satisfying to him when he got larger.
His mommy, my daughter, had the most awful colic for her first 6 months, and I would walk with her for 4 hours every single night. We were both miserable if I tried to put her down. But then it simply stopped. She couldn't hold enough in her tummy to last even 2.5 hours between feedings, day and night, for her first 8 months. So I co-slept with her, and when she woke at night, I would let her nurse while I dozed. It was a lovely solution for both of us. When she no longer needed night feedings, we still enjoyed the co-sleeping until she was nearly 2. She had no trouble at all switching to her own bed, so I did not create a problem by giving her what she needed while she needed it.
I guess my point is that you won't really know what's going to be needed, what's going to work the best, and whether you will form habits in your child until you are looking back on past history. Some parents swear that babies will get hooked and needy if they comfort them too much. I think they read that in a book, but it doesn't seem to be a fact in any of the young children I have watched grow up. They need what they need when they need it, and then they grown bigger and their needs change.
Older babies begin to need more space, more choice, more freedom. Just like with swaddling. Very few babies do well being swaddled after their first few months, even though they may not have been able to sleep without it when they were tinies.
Do whatever serves you and your son the best while he's still little, K., and I think you'll both be just fine. You might also want to invest in some good books on parenting kids at different age levels. The Happiest Baby and Happiest Toddler on the Block are good ones for moms who want to be emotionally comforting to their babies. www.askdrsears.com/ is a very good site for all sorts of parenting tips. Look up on the internet about attachment parenting for loads of supportive information.
You'll get warnings from strict parents about spoiling your child, but as long as you are clear, consistent and age-appropriate in your boundaries and expectations, that won't happen.