It depends. Smaller, younger trees take longer to mature, but they're more resilient, their roots don't get as damaged during transplanting, and they recover faster. Plus, they're much more affordable to plant, and it's possible to DIY the planting. 

On the other hand, mature trees produce fruit faster and provide more shade and privacy immediately. Ideally, a small or medium tree is the better choice if you can wait a few years for it to mature. But if you need immediate maturity, a larger tree is the only option.

You should avoid cutting off the top of mature cherry trees. This process is called tree topping, and it’s not recommended for cherry trees—or any trees, for that matter. Tree topping removes between one-third to half of the length of the tree trunk, resulting in structurally unsound, fruitless suckers. The only exception is for saplings. Young pie, sour, and tart cherry trees that are over 30 inches tall in the fall or winter before the tree blooms can benefit from heading cuts.

Trees aren't big fans of moving, and they do go into shock during a transplant. Although most carefully thought-out tree transplants see the tree recover from the shock just fine, there is always a risk of having an unsuccessful move. Proper preparation, timing, and diligent aftercare are crucial to minimize the risks when transplanting a tree.

Generally, you’ll want to prune back the trunk by 1 to 2 feet each year to promote bushy growth. Doing so concentrates vegetative buds closer to the bottom of the tree, where you can easily harvest fruit. For side shoots that are a year old, leave at least six leaves. 

Never remove more than 30% of a tree’s foliage during pruning—even if your tree is really overgrown. Removing this much foliage at a time could kill your tree.