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I'm familiar with Apple Barrel paints, I've been toying with whether to go with those or Model Master enamels.
Guys, I would be wary of using hobby paints. If you really want your work to last, spend a little extra and get a true artist's acrylic. These normally have less catchy but more descriptive color names like "Titanium White" or "Cadmium Yellow" and are designed to be lightfast (i.e. the colors will not fade over time in exposure to sunlight) They will typically have a lightfastness rating on the package. You will have to do more mixing to get the colors and consistency you want, but the results will last longer. Acrylics will still crack over time, but there are some textile acrylics (often designed for airbrush use, like Golden or E'Tac) that have a good reputation for using quality pigments and should flex well with the leather. Make sure that you give the acrylics sufficient time to cure before wearing. Acrylics dry rapidly, but are not fully cured for days, and will not be very sturdy until they are. (Heating accelerates this process, but it is problematical to iron a leather jacket, so have patience). Putting paint on too thick, or leaving too little drying time between coats, will encourage cracking.
If you are going for an authentic look, then hand-painted hobby enamels are probably the best, since that was typically what was available to aviators of the 40's. But they will likely age the same way vintage jackets do, which means inevitable fading and cracking.
There are a few paints and dyes designed specifically for leather, but I have not tried any of them. A good leatherworking site may have more info.
If you want to paint something that will last as long (or longer) as a well cared for leather jacket, then spend the money on a good paint, and prep the leather properly. Also give careful thought to clear coating. I've seen a few schools of thought on this, and I've seen a few disasters. I personally stay away from rattle can clears and just spray a few extra layers of transparent acrylic medium. Some people like to use polyurethanes, but a poor choice can lead to cracking and yellowing. (They are also very toxic, so be safe if you spray)
Cracking can happen to anyone, since there are a lot of variables that can influence paint adhesion, and many are difficult to control. But fading is a known evil and can be avoided by using time-tested pigments. Spend the money and get a paint with pigments you can trust. Do your research. Most paint lines have both good and bad pigments. When in doubt, buy the expensive stuff.