I do not pull my carb bowls at the end of their seasons. I just run stabilizer. I have never had a "surprise" problem at the beginning of the next season, with one exception.
My generator had sat for months, and I'd closed the fuel shutoff and ran the carb dry at the end of the previous use. I'm pretty sure I was using stabilized gas, but this carb was already somewhat when I bought it, it needs partial choke to run smoothly. When I went to start it the next time, it wasn't starting. Then I looked and saw fuel pouring from around the carb. I closed the shutoff, and started removing things to reach the carb. I decided to tap it a few times, and try again. Opened the fuel shutoff, got it started, and it was fine.
My theory (not proven) is that the float stuck to stuff at the bottom of the empty carb bowl. With the float stuck to the bottom, the needle valve wouldn't close, hence gas pouring out. But as I started disassembling it, and tapped the carb, maybe that helped get the float free from whatever it was stuck to, and then it was OK again. Again, this is just my theory.
Apart from this incident, I've had success with running the bowl empty, with stabilized gas.
If you're comfortable pulling the bowl off, there's certainly no harm in cleaning the bowl out.