I agree, and not just for commuting. I started here years ago when I wanted to buy a bike and learn to ride, and I was overwhelmed. I bought a used "big box store" bike and the more I read BF, I was ashamed. So I bought a "real" bike just to feel legit. It was more money than I'd spent on anything at that point, and I was so afraid to have it stolen that I ended up riding the cheaper bike most of the time. My expensive bike has probably been outside 3-4 times in the 7+ years I've owned it.
When I moved cross country, I could only take one bike, so I now only own the "expensive" one and now that I'm thinking of riding outside, I'm worried again. I sometimes wish I still had that gold old 'cheap' bike.
At the time, I remember considering a "mid range" bike at a sporting goods store--maybe 2-300$US. I couldn't get it out of my head that tons of people on this site swore up and down I'd be failing at life if I did not buy from the LBS instead. I was in Boston so of course they were all massive a-holes at those shops, and it totally sucked giving them my money but I did.
I am "stuck" with what I have, and I know I have been "held back" from riding outside for the last couple of years because of the worries surrounding having everything "right" and of course the theft thing. Even now, I've tried to go through all the motions to get it outdoors, , and I wonder whether I'm just better served renting or doing bikeshare.
I wish I had never spent that much in the beginning. If I ever did it again, I wouldn't and I'd never tell anyone they need to spend a ton to get started.