Two puppies can definitely be more difficult than one. The puppies will tend to bond with each other and not with yourself. This may not happen in your case because you have already had Winston for a while.
If you do get them both it is very important than you spend one on one time with them individually and make sure that they are used to being by themselves.
If you do get them both it is very important than you spend one on one time with them individually and make sure that they are used to being by themselves.