This is gonna be a long-ass post, so I'll split it up, heh.
I thought Jalen said he left law school, not law job. But I went to the game again after your message and you are right. But that makes it look older, not younger. At least 22+ years (and the way he said Pops didnt like he left that job, and after all he fought to stay away from that world I think years passed and he probably is closer to 25 than 21 (this is my guess hahaha, but as you said, no real evidecen yet).
The "lawyer job" can be very much subject to interpretation.
On one hand, it could mean Jalen was a full-fledged lawyer by the time he gave it up as you said (placing him much older in terms of age), but on the other hand, as I've stated before, Jalen could have just been a legal intern (and yes, internship can be considered a form of employment, depending on the work that is being done.
Also, minimum age for internship varies depending on the country. While common minimum age of internship for a law office seem to be 18 or 19, I've even seen online some claim they hired high school students who were 16 or 17 years old.
Here is the possible scenario by me:
After graduating high school, Pops pulled a lot of strings (through bribes, threats etc) to get Jalen an internship with a prestigious Law firm (which requirements to get in are very high), to get his son away from the Family business.
Jalen spends around a year or so learning and working for the firm for the internship period, but he hears of a mole in the Family so decides to come back getting the title "The Returned Prince."
So it can work even with Jalen at a younger age.
About MC being scouted, I didnt say they leave him after the Luna event, just that makes sense taking a pause at that point, and when MC father left and Rina started acting less motherly. Remember Guildart asking if he needed to intervine or not to Wilfred just because some kids were beaten MC, that can be expected, so if Rina is harming MC its hard to believe they will not care enough to intervine (it can be a risk and they can lose him).
With MC, I find it harder to believe the Family (especially Wilfred and his intelligence network, which I'd say is not eclipsed by most Families) would put a pause on it at My name is Luna flashback point though.
If they started having surveillance and intelligence gathering on MC from before Luna was taken, then I find it it makes more sense for Wilfred's intelligence team to continue working on that to some extent even during the time of Luna's abduction.
Cordia may say "all hands on deck", but I can see Wilfred leaving bare essential personnel & resources to keep track of MC (more resources allocated to finding Luna, but still continuing to keep tabs on MC).
This for me, feels like more likely actions Wilfred would take, instead of putting pause on surveillance/intelligence on MC for 7 months (period which Luna was taken), and come back after that period to find out his information on MC is outdated (as considering he's known to be pretty darn thorough in pretty much......everything, stopping or pausing on surveillance/intelligence on MC just seems out of character given what we've seen of Wilfred in the game).
And Cordia wasnt the only one acting to find Luna, remember that even Wildred feels attached to the girls, so even if he can, its hard to believe he will not using all of the resources to find her.
What Im trying to say is that in some numbers the events colide more than in others. It isnt impossible, just harder to explain.
But I made the timeline so if we find more info supporting that theory we already made one.
With Wilfred, yes he has attachment to the girls. But you've also got to remember that Cordia wasn't acting rationally during that time (which is understandable given Luna was taken away. She was 100% emotional, and threw away her rational side she displays most of the time).
She was basically willing to burn all bridges (Wilfred's own words in My name is Luna event) to the point of being reckless.
So I can see Wilfred being a Jiminy Cricket to Cordia during this period, and even hold back some funds and resources for other endeavors should he believe resources being committed to them are justified.
And given Wilfred puts the Family (not just the core Family members but the organization as a whole) above all else, I really don't think it would be out of character for a side "off the books" project.
Just because Finding Luna is the primary focus of the Family during that period, it doesn't necessarily mean that would be the only thing on Wilfred's mind (or only thing that he would be doing). He just wears far too many hats and bears too many responsibilities to be focused only on that one issue (Luna being taken by M6) despite caring deeply for Luna and Gracie like his own Family.
That's how I see Wilfred during that time. Being attached to Luna and Gracie doesn't necessarily pull him away from his other responsibilities even when she was taken.
In fact, him still getting involved in other matters (to lesser extent than before, due to the circumstances, but still undertaking them) compared to Cordia who would be thinking about Luna and nothing else I think does bring a good balance of how DeLucas would have handled ALL matters during this Luna abduction time (I mean, given Cordia's state during that time someone else in the Family's top brass would have needed to stay rational).
That doesn't mean Wilfred cares any less for Luna just cause not 100% of resources were used.
It's just how Wilfred (I feel) is as a character. He just has too many obligations and responsibilities for the Family as a whole and is less inclined to act emotionally than rationally.
But all in all, nothing is yet set in stone, so we'll see how it all goes, heh.