This is gonna be a long-ass post, so I'll split it up, heh.
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.
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on MC for 7 months (period which Luna was taken), and come back after that period to find out his information on MC is outdated (as considering he's known to be pretty darn thorough in pretty much......everything, stopping or pausing on surveillance/intelligence on MC just seems out of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).
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.
About Jalen age and job, as english isnt my mother language I wasnt sure if they call an internship something around the lines of "job" or "employment", but Ill take your words and star from your idea. But I think it was Jalen we wanted to leave this world, so its hard to me to believe he would accept Pops using his contacts, but aside that if the word means what you said, then it could have around 21-22 years old.
About Wilfred scouting, this depends a lot in who gave the order. If Wilfred was scouting you because Enigma ordered then yeah, there is no point in a delay, because Enigma and DeLuca arent the same thing. But if was Cordia or the DeLuca who did it, then I think it makes a lot of sense to a pause because of Luna. And if not because of Luna, because of whatever happened with Mc father and mother at his 10 years old.
So when i think why they were scouting him, and using the info your guessed last time (MC age after looking at the picture of the memories of Guildart) then MC was with his mother and father around (maybe not in home all the time, but some times) and why scouting him? Was MC a genius like Gracie but in other way? Or was that the contract or a promise between Rina and Cordia?
If Rina saw that MC father could become a threath to MC, then it makes sense she went with Cordia, even after turning her back, and asked her to protect him. And the only possible way would be making him part of the family, but until that moment watching him in the shadows (and this makes sense about Serpent telling you "we were wating you since you were a kid"). You crearly had talent, but as Guildart said, maybe not Serpent potential, so the only reason I see to wait you is if it was planned/asked when you were born.
And then, if we follow what I said, it makes sense to pause or change the method afther something happened to MC father since he left, and his mother changing her method because of that (like rushing things). Then MC went to Pops protection for some years, and at some point I believe something happened that made them choose to take him with the family. And this makes sense if we remember what Serpent said about "when you know the reason of your contract dont be too harsh", because thats the kind of answer that someone gives when they did something to protect others.
So, in conclusion, if Rina changed because of what happened with MC Father, then maybe Cordia (assuming she was in charge) could ask Wilfred to stan by for the moment. But even if there was no pause at all, then narratively its a big coincidence that all happened in that little ammount of time (as I said in one of my theories, that if all happened in the same 1-2 years, then it implies some kind of connection).
And one more thing. If MC has 23 years, then when Luna (6) was abducted he had 10 years old. And MC father left him, and at the same time we see Luna being abducted and a strange man around there, that has some personality traits as MC father.
So, what if Rina understood that MC Father was going to do something like that and she started preparing MC because of that. And what if thats what made the original Serpents broke the team, because some of them were considering making experiments in others to have better soldiers/or new Serpents, and avoid another war that way. Why Wilfred or Cordia couldnt find M6? the only one we know that can rival them is the original Serpents.
When Cordia talked about her past she does it like she was emotional at that time, so what if what changed her was related to the original Serpents, something they did to win the war, and something happened with Gracie and The Forrest that made her like her (like trials).
