Hi Jhay
WITW has smaller scenarios available so you do not have to start with a huge one. WITE is an excellent game also, like Budd said. It does depend on your theatre of choice. WITW has a new air-war element which can be turned over to your ai to control. WITW is the newer of the 2 games with a lot of new mechanics/rules. A WITE II is being worked on and maybe out next year. The new WITE II can be joined to the WITW to make a huge theatre
WITW does take some learning but as you have seen there are excellent videos, AAR's and tutorials out there. The community is also very active. Again, like budd said, the details are magnificent. You can spend hours, if you want to, just going over the stats, oob's, etc. This is a choice and not required. You can start with a small scenario and take it in small steps. You can save it and come back to it.
There is a huge amount of play value in WITW. You could play it for years
because it has so much detail and a great selection of scenarios. You could also play it P.B.E.M. against a human opponent
I would consider purchasing the game from Matrix. It gives you a stand-alone version as well as a Steam Key. More money also goes to the developer. The physical copy might be of interest to you as it comes with an excellent hardback manual. The only flaw is that the game is constantly being updated so the manual changes. It is easier to change a PDF.
Matrix has been having a few sales recently so you might want to keep an eye out.
Ultimately, this is an excellent wargame which does require an investment of time to get the best out of it. If you do have the time, you will be rewarded with a rich, immersive experience for years to come.