I have successfully taken rose cuttings with both new and old wood. It is important to let the new stems sufficiently mature. The new wood is usually mature enough after the stem has just finished blooming. If you don't let the stem mature enough, then it usually becomes limp and will die before you can get it to root. I take cuttings from new rose stems in the spring right after the first bloom cycle. Then in early to late fall (in Southern California) I prefer to use more mature or old wood. When using old wood in the fall, I will remove the rose cuttings from the Mason jar, baggie, or mister, after only several weeks since it is cool enough then for them to root on their own as long as I water them daily.
Allow rose hips to develop by leaving dead flowers on the plant. The flowers are typically pollinated by insects, or pollinate themselves in some varieties, so there is no need to pollinate by hand unless you are breeding specific plants together. Leave the flowers on the rose plant without cutting them. After they wither, small fruits known as rose hips will develop in their place.
Prepare a large hole. You'll need one for each rose bush you're planting. Use a garden spade or shovel to dig a hole 18 inches (45.7 cm) wide and 18 inches (45.7 cm) deep. The measurements don't have to be exact, but a hole this wide and deep will be suitable for most roses. Mix the soil you removed from the hole with compost, and use some of it to form a small mound in the base of the hole. Add some bonemeal or rose fertilizer.
Cover the cutting loosely, pot and all, with a plastic bag or plastic wrap and keep the soil moist. Putting a tall stake into the pot will hold the plastic away from the leaves. If the plastic touches the leaves, they remain wet and can succumb to a fungus disease. Along the same lines, make sure the condensation can escape from the plastic or the stem will rot.