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I was praying the Rosary recently and came upon the Presentation mystery. It occurred to me that it's a type of the Mass, God the Son being offered to God the Father.

That's one fun thing about the Rosary. You can pray it for years and still get a fresh insight.

What are some insights you've received?
Only a big personal insight, and that is to be patient in all aspects of my personal and work life when I contemplate on the third, fourth and fifth sorrowful mysteries.  Patience is a virtue, we heard this quite often, but because I am so impetuous, and prone to resolve concerns rashly when more prudent thought and less action would’ve served me better during these trials. One cannot always look for easy or immediate resolution to our burdens.  I now often times contemplate upon this when things are going astray.
I've always liked the Finding of Jesus in the Temple. Tons of symbolism there. For example the three days that Mary & Joseph look for Our Lord is a prefiguration of the three days Our Lord would be in the tomb. That Our Lady would almost be searching for Our Lord for those three days and then he to say did you not know I must be about my Father's business? To give a preparation that all of his Passion and Death would be because he would be going about his Father's business. In a similar way going about his Father's business could also work with his ministry that he would have to leave Our Lady and go to teach and challenge the Jewish elite (which to a lesser extent was how she found him in the temple) and as such would be doing his Father's business. Of course in this first time Our Lady at least had St. Joseph to console her, in the next time she would not.  Lastly we see that Our Lord made himself subject to them. To think that God allowed himself to be subject to men.
The idea that in the Visitation, Mary carried Jesus to everyone and we also have Him living in us so that's an image of what we should do.. even though He is not present in the exact same way
The most poignant insights have to do with Jesus' sense of humor. When they say man was made in God's image, they weren't kidding! Corny puns, especially!

A great theologian pointed out to me Jesus' use of double the talk about the camel and the eye of the needle. The word camel and cable are the same word or homophones in the original language. Jesus was using a pun, a play on words! Now when I read things in scripture, I look at it with this knowledge in mind and have had such a deeper insight into God's personality. It takes Him out of the academic, and helps me to understand that He truly is a living God. Frankly, I don't see how a person has a relationship with solely an academic understanding.
I was at Eucharist Adoration a few weeks ago. I was praying for guidance on what to do with all the confusion in the Church. I was told  "Do not waver in your faith". I haven't told anyone. I'm not sure how to do this either. The parish I belong to is not a traditional parish by any stretch, but It's not liberal either. I have been attending Devine Liturgy at a Byzantine Church. It's  about an hour away once a month to keep my sanity. There is no TLM near me at all. If anyone has any suggestions I would appreciate it.
Meditating on the carrying of the cross and the crucifixion helps with with perseverance and staying calm. I forget where I read it, but most crucified (or similarly executed) people tended to go mad from pain and thirst, wuich led to them shrieking out obscenities and blasphemy. Christ did neither, and bore it with dignity, if that’s the right word. This has been an enormous inspiration to me when dealing with life’s struggles.
When meditating about the passion narrative today, I noticed some interesting parallels between the nativity and the laying of Jesus' body into the tomb:

-Both events take place in a cave

-In both events, the persons taking care of Jesus' body are named "Joseph" and "Mary". (Joseph of Arimathea and Mary of Magdalene in the latter case).

-In the nativity, Jesus is wrapped in swaddling clothes, after his death he is wrapped in a linen cloth.

- During the nativity, a star (or comet) is hovering over the cave. After his death, a huge stone is moved in front of cave. It's as if the star/comet had fallen down on earth and lost its light.
Lately I keep finding myself focusing on the virtue of humility, and so many examples of Mary and Jesus' humility in the Rosary.  From Mary's Fiat, to Jesus' birth in a stable, Jesus accepting Mary and Joseph's authority oi the Finding in the Temple, all the way through to the Sorrowful Mysteries.  Today I find myself pondering the Scourging and how that punishment was used on the lowest of the low criminals, and of course the Crucifixion.  I try to open myself to ways to be obedient to God and humble myself to serve others.  
I had interviewed and applied for a job that would have been wonderful for my family, it was as an RN in a clinic 2 miles from home.  I prayed about it daily, I'm at a job right now that I used to love, but unfortunately there have been changes that I feel make my role more money-centered than patient-centered.  The interview went well and I was very excited.  Yesterday I got my answer, I would have to participate in sterilizations--vasectomies, Essure implants, etc.  Needless to say I'm disappointed, but I'm thankful Our Lady made it clear to me before I accepted the job!  I got back on the job search and found several openings for Community Outreach with the VA.  We're a military family and I've always liked working with veterans.  I will keep praying, maybe this is the direction Our Lady is pointing me in.
I often think of the contrast between meditating on the Crucifixion, while saying "Blessed art thou among women". Also, while many secular humanists would find it ghastly and morbid, it's so comforting to hear a child say "Holy Mary Mother of God, Pray for us sinners, now and at the hour of our death".
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