For us, we started out on our journey about 1/2 way through my pregnancy with our first son. I knew I needed an alternative to disposables because of the cost factor and had some friends that cloth diapered their kids, so I started asking questions and doing more research. It was pretty evident early on that we needed an option that wouldn't cost a lot to start up and we weren't terribly concerned about the ease of use since I was planning to stay home with my son and didn't mind the extra work. It helps to note that my husband was on board with all of this and also didn't really care about how easy the system would be to use.
There are tons of sites out there to do research on cloth diapers and compare prices, but I ended up ordering from Cotton Babies and we decided to start with prefolds, Dappi covers (the pull-on nylon pants), and Snappi's as a closure instead of diaper pins. So for little out of pocket expense we got ourselves set up to start.
We waited a few weeks after Carter came home to jump in (we had a lot of disposables given to us at showers and so we used those during this time). Once we started, we quickly got the hang of things. There is a learning curve and I did a lot of research on different ways to fold the prefolds for maximum absorption, but it really wasn't too bad. The laundry was also a breeze! Since I was exclusively breastfeeding, everything just went straight from Carter, to the diaper pail, and into the laundry.
Once we had the hang of things I started looking for other kinds of diapers on sale. We got some all-in-ones from a garage sale and some "seconds"/clearance of the BumGenius 3.0's from Cotton Babies (TIP: seconds may seem like a risk, but they have been wonderful for us...a great way to try new diapers without the sticker shock of buying them brand new). I eventually also bought some hemp liners for my BumGenius diapers that have been WONDERFUL! I found some homemade diaper wipes from a woman on Freecycle and bought some BumGenius wipes from a garage sale (I prefer the homemade wipes which are mostly just flannel and are super easy to make on your own).
A few months ago Cotton Babies came out with 2 new diapers, Econobum and Flip. I was interested in trying the covers with my prefolds as the dappi covers have to be purchased in each size and these covers were one-size (meaning they adjust to fit your baby from birth to potty training, generally). I found some Econobum covers being sold in their clearance section and bought a few. Well, me and my husband LOVED them! They were so much easier than Dappis, and since we bought them on clearance the price wasn't too bad either. When they went on clearance again we bought enough to diaper our son and the baby that we were expecting (due this October). We also got, via a trade on Craigslist, some fitted diapers that would work for a wide variety of sizes and we really enjoyed them. We are currently on the lookout for another brand of fitted diaper to use with Carter as he gets bigger and to add to our diaper stash for the new baby as well.
Overall I have been incredibly happy with cloth diapering! It hasn't been too much extra work and I'm not a slave to the system. We still use disposables at times when I know I can't keep up with cloth (when I'm sick, baby is sick, or we are traveling a lot) and he is usually in disposables when we go out of the house or to relatives. We don't expect other family members to cloth diaper him, we have disposables available for these times. I'm still frustrated at finding a good cloth diaper for overnights as our son is a pretty heave wetter, but I don't mind using disposables for these times either. Hopefully in the next few months we will be adding to our stash and, as we do, I will try to update with any new products that we try.