The smaller the shuttle, the nicer it may feel in your hand. A larger shuttle, having more weight, gains better momentum over a wider warp. A lightweight shuttle is easier on your wrists, if your project doesn't demand something bigger.
Which quills do I use with which shuttle? It's all about resistance, and how much tension you want on the thread as it exits the shuttle. The best approach is to experiment with several shuttles and different quill sizes. There is always one combination that is clearly the best one for any particular project, and sometimes you just don't know until you try it out.
Here are some basic guidelines:
The shorter the quill, the more play it has inside the shuttle box, creating less resistance and tension as the thread exits the shuttle.
The longer the quill, the less play it has inside the shuttle box, creating more resistance and tension as the thread exits the shuttle.
If your selvages are too loose, you probably need more tension on your thread as it exits the shuttle.
If your selvages are too tight, you need less resistance and tension as the thread exits the shuttle. (You might also need to be using a temple.)
Your skill at winding a quill has everything to do with how evenly tensioned your thread exits the shuttle. See the bobbin winder page for Becky's vintage MiniMovie on winding a quill.