I will agree, makeup is a difficult skill to acquire. It takes lots of practice but the learning is much easier if you have a teacher available. For me, my primary resource was/is my wife. Dena's advice of finding a cosmetics store is probably one of the best steps you can take. They can match your colors and show you some basic looks that work for most any occasion. One issue that I have not been able to get good help for in normal Cis gal cosmetic stores is dealing with beard shadow. If you are fighting a strong dark beard, there have been several threads on Susan's that could help. I imagine many here have great tips for what has worked for them.
My suggestion (just like Dena suggested) go to the pros at someplace like Sephora's, Mac or Ulta. They really know their stuff and can teach you as they go.
Get a basic look that works for you and is fairly low maintenance, easy to repeat. For me, it is my day look and includes; basic foundation, eye shadow, mascara, a touch of blush and lipstick. I have it down to 15 minutes tops (yes it took me a while to get there). Once you get that down, start playing with new looks, the eyes are a great place to start expanding on. You really can't go wrong, if you don't like it, wash it off and start over.
Enjoy the ride. - Anne