when should I stop attempting the 4-move/scholar’s mate?

You’re not developing your skills by playing the Scholar’s Mate. The sooner you get to practicing using the opening principles, the better.

When you are serious about improving.

i was told from the start to not go for trick checkmates when learning chess and I'm not even close to good yet.

Now

I just show it to my students and show the counter. I advise them not to develop pieces that way though.

I've found it useful to practice the scholars mate a lot and a lot of those early queen attacks just so I have a quick understanding of what to do against them when they're used on me.

now.

on a side note, how would one "transition to the scholars mate from the italian game"

the nf3 is blocking the queen 

I don't mind my students using the scholars mate in their progression, it helps them to understand that they need a plan, and that a bad plan is better than no plan. However in time they realize they need a better plan, the Italian, in particular the Fried Liver is a great transition as it keeps with the theme of attacking that weak f7 square. Once again, they move on from that when they realize their plans need to mature and become stronger.

Good Luck!

you play 2.Bc4 first instead of queen move. If the second player plays 2...Nf6 then you can transition to Vienna Opening with 3.Nc3 and possible followed by f4 depending on how your opponent respond.