Lots of people let wet weather deter them from riding. They think it's going to take a lot of investment to get all the right stuff for sloppy rain commutes. Here's a few quick thoughts from my senseless mind.
Nice bags are great. Mine were expensive (to my standards) but would last me the rest of my life if all I ever did was bike commuting. There's almost no chance that water would get in there. But you don't have to spend that. For years, I had cloth bags that I used with my clothes inside a rolled up garbage bag. I don't think anything ever got wet. Go for it. You may love riding in the rain. If you love it, invest in some nice bags. It's worth a try.
For wet weather attire, I wouldn't go crazy expensive. It was 39 degrees this morning and I rode in a pair of Walmart sweatpants. My rain jacket was twenty bucks. I've been wearing a Buff over my face to keep crap from flying into my mouth. It doesn't really keep me warm. It's just deflecting nasty road grit.
Should you ride your bike in the rain? I would probably tell you to try it. If you try it and realize it's something you may do more of, maybe think about a single speed beater bike. But a few rides a year won't be terrible. Keep your chain lubed if you give it a try. But don't be terrified of riding your bike in the rain.
Just give it a try. You don't need a whole lot to get out in the rain.