In samatha one can judge their progress through the progression of jhana, is there a concrete/measurable way to judge progress in vipassana?
Taking Dependent Origination into account the main issue leading to the conditioned existence is when we sense any sensations due to, we react with with like or dislike which you try to possess or get rid of. This keeps you rolling in stress and conditioned existence. Once you feel the sensation and you maintain your equanimity then you stop conditioning. Therefore by all means the best measure of your progress is much equanimity and awareness you have towards feeling and sensations that arise in different situations. At a more advanced stage when your equanimity is not wavering, the main measure can become how much of the 3 characteristics of existence you can see. At some point your will start seeing the arising and passing away of phenomena in any place of your body confirming everything is in a flux of change. You will realise any feeling you get has a finite length. It arrives as cluster of vibrating quantum particles and stays for a finite duration. You have no absolute control over creating, maintaining or the sensation of a particular sensation.
The next way you can monitor your progress is through your wellbeing and that of others people around you. You will be less agitated and stressful. This intern makes people around you less agitated and stressful. You become moral. Each time you try to generate negativity you see the process of stress and agitation building in you. This re enforces your morality and cordial interaction with others. You will have a balanced mind thus make the right proactive decisions than emotional reactive decision. This will be profitable for you in this life and the afterlife for you and everyone around you. Also you will experience peace and happiness with in you. As always your 1st measure of progress should be equanimity and mindfulness after which is firmly established you can look at the secondary measures. You will actively investigate the phenomena arising and passing away within the framework of your body. Once well You will feel pleasant and relaxed. Your mind will get focused. You will have a lot of energy in you.
Another way to measure your progress is through the level of understanding of the Noble Truths at the experiential level (Paccattaṃ veditabbo viññūhi). If you were to use another way to investigate your progress you can keep looking at sensation within you. In further investigation you will see that any stress or agitation arises arriving in you. On further investigating you will see what causes this is your attachment and aversion. You will start seeing if something happens to something you identify as me or mine (things, ideas, thoughts, views, body, friends and foes) you get either agitated or pleased. The lack of mindfulness and equanimity you grasp to the feeling that arrised when you sense something. (E.g. your foe losing his job.) You always long for similar incidents as when you get to know and recognise this is in deed your foe then you experience the some feeling. As you practice, you see when your get any volition in your mind, you experience sensations. You see the sensations as not permanent, grasping to them cause resentment and not absolutely controllable. When you are equanimous and mindful in all times you see that this reduces the stress and agitation in you. You will see every time you even think about breaking your morality you get stressed and agitated, more control you exercise over your mind and prevent it going into negative states more positive you feel and when it does go agitation and stress arises, you will see each time you like or dislike towards something (starting with a certain type of feeling) you loose your balance of your mind and craving to create any such sensation or feeling is not under your absolute control, does not last long and since it does not last it is not satisfactory. You see the way out of this is not to react to the sensations you experience but be aware looking at their true characteristics.
Also you can always be mindful of the defilements to see what frequently arices and how intense they are.
Monitoring progress is has its drawbacks. Proximate cause of looking at progress is striving too hard. You have to leave the results for itself to manifest in due time than be trying to be over mindful of the progress. If you are looking for progress too often then this is a sign of being too attached to the outcome thus losing the balance of your mind and falling behind in your practice.
You do occasionally (not too often or not too far paced) have to see how you are doing though. This is to see if you are doing the right practice and on track. If you are not making progress then the this might mean that you have missed some aspects of the practice or doing something wrong. When you do look at progress is that if is like a knife. You cannot see the daily wear and tear but suddenly notice that it has worn out though this was happening little by little over time.
Eradication of sanskaras of craving and aversion, I'd say, is a good way to measure one's progress in Vipassana. Earlier I used to get upset with something and remained disturbed for one week, but after practising Vipassana for 4 hours daily for a month, now I get over with a similar turn of events in three minutes.
So, I could see very tangible progress in this path - hence I've kept up my efforts, though I am not always able to keep up that high levels of practice ... but I am highly motivated to keep working hard ....
well theres a couple of ways... 1- you could study more about the stages of insight and enlightenment, and 2- you could practice with a monk regularly and ask for help.
Im sure there are other ways (and feel free to explore them) but these are traditionally how progress is made and verified in buddhism to he best of my knowledge and really, if you want to know how you're progressing on a buddhist path... theres only one type of person likely to be qualified to evaluate you (though not all monks are valid choices).
Here is a video my teacher made on the stages of insight through vipassana though for a short run down so you can make a general assessment. https://m.youtube.com/watch?v=G3u4JEEdK1Y
Suminda concludes in another answer.
When you do look at progress is that if is like a knife. You cannot see the daily wear and tear but suddenly notice that it has worn out though this was happening little by little over time.
I would take this thought further. It describes the appearance of awakening. We don't add something, but we wear out something we never had.
The insights are a tool, a horse that trains us to be a good rider. When we get to the ocean we have no need of the horse. We sail on the waters of tranquillity.
Then what? Go down the other side of the mountain and live what we have discovered as our original mind.
These are not concrete in the sense of physical appearance, but when you start "wearing the knife down" there are noticeable changes in clarity of perception. At first they are fleeting, but with continued persistent and compassionate practice, the clarity of perception becomes something we no longer need or want to strive for. But seeking clarity for its own sake or for the sake of personal delight is an impediment. Putting clarity to work as a tool to help all by first clearing our perception and then living as an example of simplicity and awakened joy will speed this part of the journey.
The yardstick to measure progress is by sensing your volition to serve other people. If it is increasing you are on the right track.
Also if you are caught in the same situation as you did previously but acted In a calm and balanced manner, for your own benefit and benefit of others, you are on the right track.
If you got angry before and it lasted for several hours, has this period reduced? It eventually reduces as you tend to come out of your miseries quicker. Same for lust, hatred, jealousy etc.
-S.N Goenka (ten day discourses)