When the thing with the car heppened at the beggining of the game it was Wilfred who was driving. I know that you are an important person and the wanted you to be in a unique position living inside the house, but just follow me a bit.
When the food situation happened (i need to replay this part too) it was inside the house but only your food was poisoned, and the amount of people living in the house isnt that big, so Wilfred is in the house too.
When the situation with the assault happened, it was Wilfred who, saying that it is a punishment for the girls, told you to go with them to this strange place (in a supposedly peacefull place) for a few days, with almost no protection. We can say there was a mole, but it was a really strange punishment that included you.
Then again with the situation with Eiza. This one can be a different matter, but then again, someone can came into the house and threaten the life of anyone just that easy? or Wilfred allowed this? and Wilfred came to make jokes when there was an assassin inside the house when he is responsible for security?
Im not saying there isnt a threat in your life. But Wilfred is connected to A LOT of things that happened, in really strange situations. Then again im with you in that he is moving the strings in some things with the girls.
I have 2 theories:
-Its that easy to come and kill Cordia or the girls and the security around the big families isnt that big. So even if Wilfred pulled the strings in some matters, all that happened wasnt that strange or unusual.
or
-Wilfred (at least, alone) was trying to """test""" you. Why "test" is the word im using? because if he wanted to kill you it will be realy easy for him.
But if with everything that happened its hard to believe that a smart woman like Cordia believes in coincidences and didnt see Wilfred is involved. Thats why i thing that, in some matters, and with the reason to protect you, she allowed him to do some actions to develop your skills and character. I believe that there and and will be threats to your life, but i think that you will be part of this world no matter what you want, so they are trying to force you into understand the dangers and be prepared for them (related to your mother, or no matter the motivation).
With the driving, yes Wilfred was the one who was driving. But I don't think that necessarily points fingers automatically at him as the one responsible.
Because let's not forget, Joey was the one who was initially supposed to drive MC, not Wilfred. Also, there were Dominico and other Soldatos training in the main DeLuca mansion's front yard.
Now, that's not to say I'm necessarily thinking Joey, Dominco or any of those soldatos are responsible for the brakes.
But that means that the main DeLuca mansion, while only main Family members (Luna, Gracie, Cordia, Isabel, Antonio) may live there (Hopes previously confirmed Wilfred doesn't live in the main mansion, but he has his own abode which is separate from the mansion), DeLuca soldiers who are not main Family members can still visit and hang around without much restrictions, whether it's for work or not.
That leaves the number of potential suspects far more wider than just Wilfred I think (basically, any DeLuca soldier can potentially be the second mole, not just Trino).
With the poison, it's very difficult to balance just the right amount of poison not to kill the MC (DeLucas wouldn't know just how much of a dose the MC was exposed to as a child, and how his immunity would hold to future poison attempts). Even a slight wrong dose, and MC would have been dead.
It's been established from the beginning how important the MC is to the Family.
Perhaps Wilfred, given his incredibly grey morals (compared to Cordia), might be willing to risk it all in order to "test" the MC (or not), but I just don't see it for Cordia tbh.
It just goes against her code of respect and honor she holds by that she preaches often to the MC and Antonio.
After the poisoning, when MC wakes up, Antonio also mentions to MC "Mother is also furious at how this could happen. It's a disgrace something like this happened without our knowledge."
Cordia being complicit, or even just aware of what Wilfred is doing would basically contradict this honor and respect moral code she holds above others.
So even if Wilfred somehow decided to "test" MC, I just don't see Cordia agreeing to such methods.
And it wouldn't really feel out of place to me either even if Cordia wasn't aware of it.
The game has already shown one instance where two of them were in strong disagreement (Wilfred thinks Gracie should start work for the Family vs Cordia think Gracie should stay away from Family Business), and I'm assuming there have already been few instances where Cordia and Wilfred have been at odds regarding decisions and sometimes Wilfred may have done things behind Cordia's back without even getting her approval).
With Beach prison event, I'm not sure I can buy that as a "test."
The girls and MC were sent to Tradimano Family (neutral) territory, and the following lines are said:
Mercenary Boss: "Our orders are clear. Eliminate the boy, leave any of the others alone, especially the girls."
Gottardo: "Leo, with his dying breath, sent an emergency signal."
Gottardo: "Mr. High Five wasn't supposed to be here. When he heard about the emergency signal he asked for permission to come too."
Just far too many things are said, actions done which I feel points it to being an actual attack, rather than it being staged.
Emergency signal, I'm assuming it's a last resort actions that DeLuca soldiers can take when they feel they're in trouble.
Don't see them abusing that for a test.
There's also the fact that both Leo and Trino (and Mercenary, depending on player choice) got killed. I mean sure, we didn't see Leo, but we saw Antonio publicly execute Trino in Cordia's office.
In addition, there is the fact that "Serpent" came to save MC with the emergency signal, and Gottardo also mentions the following:
"Most of the targets were already eliminated when we arrived."
Wouldn't really make sense for them to deceive "Serpent" given Family is already aware of "Serpent"'s closeness with MC's mother (Rina).
Not to mention there is a Cordia scene where she is genuinely grateful (if player chooses MC to opt to try and sacrifice himself for the girls to escape). Even if this was a test by Wilfred (which I doubt, given all the above, but let's hypothetically say he is), I just don't see Cordia putting her girls in harms way like that, even if Mercanry Boss received orders "not to harm the girls."
Besides, the whole event being legit threat is what really brings gravitas to the whole ordeal.
If it was just a test, it would mean at least one or two people died just so MC would have his test (which would be really, really messed up), and frankly I think cheapen the whole ordeal.
With Eiza's situation, well there is the fact that she's the heir of the (now gone) Carnefice Family, who are specialized assassins.
Their aptitude in stealth is incredibly high (perhaps even moreso than the stealth specialists in DeLucas), so I have no trouble thinking someone of Eiza's ability of stealth was able to sneak through DeLuca's mansion security (I mean even Cordia says at the end of Ombra event she can work for a Capo who deals in stealth).
And remember, Wilfred is Consigliere, but that doesn't mean he's physically in charge of every security (he's one man, and the mansion is a huge area). I'd assume the main Family mansion would have its own guards who physically stand watch taking patrols as well as possibly some cameras (And other automated security).
After Luna's kidnapping as a child by Mysterious 6, the mansion's security would be much, much tighter than before, but I think even his system that may seem impenetrable may have some chinks that someone like Eiza might be able to exploit to gain entry.
So tbh, I still don't think any of these events were really a test, but who knows, I could be wrong and it could be, or not.
Only Hopes can tell us how it all turns out later.
and I have my doubts if someone below the 'serpent' level could outmatch her these days (since she was one of the original serpents), even on a surprise stealth attack or a full-scale invasion. But, I'd like to see any of them trying! 
