How crazy of an idea is it to think about sailing my 23.5 to Catalina? Even more crazy...anyone wanna join in?

We sometimes see standup paddleboarders crossing the 18 NM to the Gulf Islands in the summer with an escort boat. Been across there at times when you could hardly stand up in our boat. In the summer, it can often be so calm you can lean over the side of your boat and comb hairs #2 and #3 in the reflection of the water.Watch the weather and go.
Indeed. When I was in high school we used to sail over there all the time in a Cal 20. Our gourmet fare consisted of pork and beans cooked over a Sterno stove, and Twinkies for dessert. (Note: Close quarters on a Cal 20 with a crew of pork and bean eating high schoolers is only for...high schoolers!)Well, if you are launching in Montana then that's crazy. If from anywhere in the Los Angeles / Long Beach area it is very sane. Smaller boats do it all the time. Watch the weather and go.
AIS could be helpful on this trip, as the San Pedro channel has very busy shipping lanes. Even with AIS you should avoid doing the trip in poor visibility.I actually have a chart plotter to install already, and I plan to network that with my VHF/AIS. Not really a huge need on Flathead, but I'm OK with spending the money on safety upgrades. Handheld radio is also GPS.
Neither of these is necessary for a trip to Catalina.Definitely take an EPIRB and maybe an inflatable dinghy.
Ed S