Looking for opinions ......
Regarding your history with the games I would leave it on the shelf.
For me, I like WITE 1 the most. It is complex and has a certain slick simpleness to it. It is perfect game design for me. You really can plan, manouver, have to have an eye on supplies, the weather and production is important, but in small doses.
WITW... I am lukewarm about it. Air War is fun, but ground war... they took the scale of WITE and it just doesn't fit the theater(s). It is too small and feels unimportant that way. You just don't have enough (ground) toys and movement is not really important anymore. Also... if you like to play the Germans it is just boring, whereas as the Allies you almost have to do too much. And even though I liked how detailed the air war is... I never got how to use it effectively. There is a point where you have so many nooks and crannies you can turn, that you really don't see what does what and how what you do can be effective. Add to that a really finegrained game calculation which is also pretty opaque, the package as a whole is off to me.
I mean somehow the developers themselves had realised it is too much too handle I guess and give the player an AI option. It is a little bit like defeat in my eyes. You design a system and then let it play itself? Also... the UI really got bogged down by the new options. It just wasn't designed that way, it is bloated.
And now WITE2... It has everything WITW brought and now even more details for the Eastern Theater. Air War, Depot Management, ground war with a lot of chits. This really is not the game for you. Even though you can leave the air war and depot management to the AI, if you will do this there is little advancement over WITE 1 for you.
My advice would be.. invest more time in WITE. If you get the hang of it, then take a second look at WITW and learn the air war system. If you've come this far and liked what you saw, then invest in WITE 2.