If you are homeschooling or just generally want to pass down an understanding and love of literature to your kids, please do not fall for the lie that Shakespeare (or the KJV Bible, or anything else that is now often called "difficult") is too old or obscure for *you* to grasp. That's how you perpetuate the lie for another generation and deprive your children of important cultural and linguistic grounding.
OP has a solid list of tips for getting to the point where you can enjoy and understand this stuff.
How I first studied Shakespeare so I could actually learn it and understand what he was talking about:
1. I listened to audio versions of the play while following along with the text. Actors provide emotions/tone to help you understand the scene. This also meant I could stop when I needed to so I could look up words or context.
2. In a 3 hour play, I would stop about every 30 minutes and watch a summary or listen to a lecture about that section. Then continue to the next section.
3. Then I would watch a performance (usually on YouTube). Lots of Shakespeare performances on YT for free.
4. Now I can read entire plays or just certain sections, and I enjoy them. I actually know what's going on. I can appreciate the language (without wondering "What the hell does this word mean?")