Start with this one (Secret), it’s the first in the series, it was rereleased later as a remastered, which is why the dates are kind of messed up:
But the above game is kind of what started off the whole thing.
Then after that, the second game is (MI2):
After that, the third game is often considered the best in the series (Curse):
The fourth installment came in with (Escape):
Then it goes to Tales, which is the one you have posted.
So keep in mind that this Tales of Monkey Island “Complete Pack” is actually just the complete set of 5 installments that were released one per month when this game was released. This is NOT all of the Monkey Island games out there.
Over at GOG, the first game is currently on sale at 65% off, and not on sale on Steam right now.
It’s been lower in price in a bunch of online store fronts, including Steam, at 75% off, so you can expect a sale on that at a later date and probably start with Secret, decide how you like it and then follow the story from there.
Do you absolutely need to know the previous stories to move on? No, absolutely not, you can jump around, but it helps to know the lore from beginning, when understanding things. I played only Secret, MI2, and then Curse. I have not Escape or Tales and cannot tell you the quality of the games, but at least the reviews are promising.
If you want to grab more than one game, keep an eye on this sub page:
As it contains games 1-4, and goes on sale often enough to about 60% off to a little over 10 dollars. Would be more gameplay and story for your money than jumping into the fifth game.
Just my 2 cents. Too bad she couldn’t answer as you wished.