[[Dear Sister Laurel, you wrote that hermits feel like novices even after living the life for decades. Why is that? I think Saint Teresa of Avila said like she always felt like a beginner in prayer. Are you speaking of the same experience?]]
Re your first query, what a terrific question --- and a difficult one too! I have never really thought about why one always feels like a beginner at living as a hermit even when one has lived this way for years (which, as I think about it, is definitely not the same as being a novice or neophyte), but I would say that a large part of it has to do with the reason we are always beginners in prayer, yes. In other words, your question is a profoundly theological one and the answer itself has to do with the nature of God and the nature of prayer.
I think the second reason is related. When God is active within us, and especially when we open ourselves to that activity, we change. Our hearts become deeper and more expansive in their capacity to love, our eyes and ears are opened to the really real (Ephphatha!), our minds are also converted, and everything looks and feels differently because we ourselves are different. Thus, through the power of God we are attuned more and more to the eternal which interpenetrates our world and this means that things are never old, never static, and perhaps no longer really completely familiar. I think that ordinarily a piece of judging whether we are a beginner or not is gained by comparing how familiar doing something is. When these things are familiar there is an ease about them, and we are able to gauge the expected results without much conscious attention to things. With prayer, however, we are constantly being brought into a "far country" and in contact with a dynamic, living God we cannot imagine much less set forth expectations about. There is a sense of adventure here, even when it is very very muted; I am not sure that adventure in these terms is ever something we are "old hands" at.
At the same time there is also monotony and sometimes a tedium about eremitical life; like everyone we may crave short term novelty and distraction, but be uncomfortable with the patience and persistence required for genuine newness. Our world often mistakes novelty for authentic newness and we are profoundly accustomed to and conditioned by this. Yet, the yearning for real newness is a part of our very being. (In the NT there are two different words for new which accent this distinction. The first is kaines or kainetes which indicates a newness of character which is superior and respects the old; the second is neos which means new in time but can also mean a denigration of the traditional or the old.) The situation of monotony and tedium is exacerbated because prayer can seem like nothing at all happens despite our trust (knowledge) that God is present within us working, touching, loving, recreating, and healing.
In the short term especially we may not be able to see or sense the changes that are occurring within us and since the hermitage itself changes very little, in worldly terms we think we are not progressing. This too can make us feel like beginners because we don't feel "we are getting anywhere". It might seem that this conflicts with what I said above about the adventure of prayer, but it is more the case that both things are occurring at the same time and we see one or the other according to our perspective. I think though, that this set of reasons (focusing on our own progress in worldly terms) is far less significant or influential for contemplatives --- and that is especially true if we are speaking of St Teresa of Avila or someone similar.