From Time to Time
It is natural to want to know where one stands with regard to achieving the goal. The Buddha suggests that 'from time to time' one should evaluate other's progress, and 'from time to time' one should evaluate one's own progress.
In this matter it becomes very important to remember that this is a system which in it's highest form rests on intentional not-doing and letting go. That means that you do not evaluate your progress by measuring how close you are to the goal, but how much of the world you have left behind.
Think about it! At best all you know about the goal before you have realized it for yourself, is the idea of freedom. Thinking in this direction you can say: I can see I am not yet free. That will be the case whether you are near or far.
What you can know that will help you judge your progress is how much of that great pile of habits you have you have managed to eliminate. That is the important factor. Take a look at how much you have changed; focus on those turning points which were a result of having seen your behavior as self-destructive.
Evaluating the progress of others in the same way will help you by way of making you conscious of impediments to freedom you might not have thought of or which are hard to see in yourself, but easy to see in others.
Reflect: "Does this that I see as a fault in this person also exist in me?"
Bottom line? This evaluation should concern itself with the yokes to rebirth:
 Is there here any idea that this body is my body? Belongs to me? Is under my control? Can be done with as I please? Do I think of it in terms of "I" "Me" "Mine"? See this with your intuitive wisdom: draw inferences from grasping or protective behavior, anger when things do not go as one would wish, etc. Is there at least an intellectual understanding of the idea that a thing that changes and is out of one's control cannot belong to the self?
 Is there here evidence of doubts about the Buddha, the Dhamma, the Sangha? Did the Buddha actually find a way out? Is this just another BS Dhamma hussle? Did he teach Dhamma such that one who follows the instructions can realize the goal for himself? Is the Great Saṅgha (Streamwinners, Once-Returners, Non-Returners, Arahants) a good description of the stages to awakening? A good example of walking the walk? You can judge partly by how far you have left painful behaviors behind; that much is a sound basis for faith. "I followed the instructions this far and this far they worked as described." You will have unshakable faith when you have seen for yourself: "All that which comes to be, comes to an end."
 Do I rely on good deeds, ethical conduct, and hocus pocus as being the way to the end of pain? Is there here a substitution of giving and scrupulous ethical conduct for self-discipline and mental development? Is there reliance on chanting, insense, candles, statues, amulets prayers, spells and wishes and other magic charms?
 To what degree have I let go of wishing to experience pleasures bound to the senses? Abandon all hope ye who enter here! Is there here evidence of ambitions? "I just want to accomplish ... before I die." "I'm not ready yet! I have more to do on my website!" Or just hankering after a good meal? It isn't all over once you have let go of sex! Have you let go of sex? Do you identify as a homosexual? transsexual? bisexual? That is a pretty clear sign that your orientation is not free from sexuality.
 Has contrary behavior (smart-ass going the wrong direction just to be difficult)? Behaviors like lies, boasting and braging, cruelty and even harm? Watch yourself carefully! What do you think all your Satipatthana practice is for? Do you whole-heartedly believe in the goal while doing everything that will prevent it from coming to be? Conflicted behaviors tell you what is going on on other levels of consciousness; you need to pay attention.
 To what degree have I let go of wishing to experience pleasures bound to material things? This is primarily desire for rebirth in some material world. The nostalgia for this world; for living in this world; to enjoy the comradery of man. Etc. Ambition to attain worldly gains; wealth, power. Secondarily it is ambition to be reborn in some heavenly state
 To what degree have I let go of wishing to experience pleasures bound to immaterial things? It is necessary to keep your interest in accomplishing the goal to the point where it has been accomplished. That is only a problem when you have reached the goal. Meanwhile what is a problem is desire for fame, magic powers, attaining jhāna, attaining one or another of the paths, wanting to amount to something, wanting to bring others into this system (it is the wanting that is the problem in this case; in this case just teach and let go of the desire to have helped (and the secret prideful dwelling on having helped) the wanting to make a difference in the world. Etc.
 Is there here evidence of unconquered pride? Looking down on others. Being a pompus ass. Striking attitudes and holding opinions.
 Has fear been faced here? Or is there evidence of avoiding the winds in the upper atmosphere? Here careless behavior points to un-recognized fears. A person who lies to keep control of his situation, never listens to others, one who can never be wrong is a person riddled with fear. A person that can admit to errors, listen carefully to others, abstain from saying what is not true is confident.
 Is there here evidence of having seen (not just understood) the Four Truths?