No, they don't have a tendency to get more infected. Most people usually start out with a very small piercing, if not a regular earring. Then they build up to larger sizes.
Generally, your ear won't go back to being completely healed. But it depends on how old you are when you pull them out, how long you've had them in, and how far you've gone. If they're pretty small, you're young, and they haven't been in there too long, you got a good shot at them closing completely.