Now as for myself, first I liked Usetawuz statements above. And will start my reply with two statements that I love. One came from my father onetime when we were talking about reincarnation. He said that how often instead of karma or to learn this or that, we just want to come back and 'Enjoy' another life! Just think of how many Simple 'Joys' there are in life to experience compared to what we are taught to focus on in life by this society.
And the other is something I heard once concerning old souls. Now one thing about an old soul is that they are a 'Slow Learner'. Ha Ha!
But now more serious things. Personally do think that this modern day society of us Human Two Leggeds might bring on some hardships that might not have been around in times past. For instance consider how with all of our increased technology, we have now become sooo impersonal to one another it seems and so divorced from one another in our daily lives. In times past it was more simpler lives with living in a community whereby we would have people around us who were loving and supporting in our day to day lives. But now how often these loving and supporting communities are vanishing in this increased techno and increasing impersonal world.
I personally feel a more advanced soul would be one who has increased virtues of the inner self like love, patience, being at inner peace amidst turmoil and troubles, wanting to help and serve others, not being so focused on the material gain of their own selves, more focused on the inner world and the spiritual then the physical, and such. And it would be those that are less advanced or attuned to be more focused on the gain of just their ownselves and things of the material world, less peace in turmoil and trouble, less love and giving of themselves to others, more focused on just the physical then the spiritual, more given to have power and control over others and of material greeds, and so forth.
Now for myself, do think evolving with our soul goes counter to that in which this present society preaches on how we must be on a everyday basis. Now take a look on some of the spiritual leaders of the past, and how often do they renounce various things of the world. Now for instance do think a more advanced soul would be one that would be more at inner peace amidst bigtime turmoil and trouble in their lives and world around them. They would also do think be one less to want to accumulate much material wealth in their own lives but being content with the simple and having enough to just to live. And then giving of the few things that do have when someone nearby is in need. They would be one who would not have to have some 'Soulmate' around them at all times. Would have various abilities in their inner selves in which this modern day society so poo poos with it's focus all on the physical. Personally do think that not necessarily they have a more harder life, but where the emphasis is in that life when it comes to a more advanced soul compared to a less advanced soul.
Now hope I have explained for do think it is hard to put into words. I think Usetawuz was right that a more advanced soul would more experience joys in the very simple things of life like even just breathing. And compared to a less advanced soul who would get all caught up in the material gain of the world with being selfish in their physical world view and focused all on their own mortal outward physical self.
Hope have made it clear. Could go on but will end here. Wishing Everyone the Best!