I was currently thinking to acquire all the Toy Story set (or at least minifigs) and with Toy Story 4 announced for 2018, I was thinking maybe I should wait to get my favorites childhood characters for cheaper if they release new sets with the upcoming movie?

Do you think it’s likely to happen? Do you see any reason LEGO would not try to get that license?

Often I wish I was out of my dark ages earlier (or that I just never had any).

I wanna say yeah because LEGO has been making a lot of Disney sets and themes lately, and now with the CMF coming up, they've got all sorts of characters. I think it's likely. We'll also have to see if they make more PotC sets with the new movie coming out.

Yeah, I think that would make sense too.

Oh and I forgot about that new Pirates of the Caribbean upcoming movie, that would be really nice to see new sets with that too. There’s been really nice Pirate ship in that line in the past.

There’s so many great license lately! I guess I’ll just have to increase my LEGO budget ;)

We can't know for sure just yet. However, I think it's quite likely - they have a close licensing partnership with Disney (to the point it seems unlikely some other company would do Toy Story construction sets, anyway), they already have a number of theme-specific molds, and it would hardly be the first time they've brought back a licensed theme from a hiatus of multiple years (what with Harry Potter, Jurassic Park / Jurassic World, Spider-Man / Marvel, Batman / DC, Mickey Mouse & friends, and Winnie the Pooh).

Similarly, I think there's a good chance we'll see more sets for not only Pirates of the Caribbean, but also Cars and Indiana Jones, whenever those franchises' next installments and/or reboots are released.