One option I would add is the app Wingz. I use it to from SFO/SJC all the time and you can avoid price spikes (you know the fare when you book) since you’re probably going to be sitting in a bit of traffic as it looks like you get in during rush hour. The other good thing is that you prebook your ride so no waiting for an available driver. Only issue I have had w Wingz is that sometimes I have forgotten to plan ahead and get a ride, so no one has picked up my request. But if you plan ahead you will most likely get someone picking up your request.

Another option would be a one way drop off w a rental car if you get a good deal. I’m guessing you’re looking at spending ~$100 on Wingz. You can price out Uber and Lyft to see what kind of rate you get from them.

I have never taken the Caltrain from SJC to SF, but I wouldn’t worry about bags. People get on w bikes. I’m sure bags will be OK.

I would highly recommend not using SuperShuttle. Its a shared van ride and depending on who they drop off first it may take you a much longer time to get to your destination while saving very little money. I think you may be able to reserve a whole van, but unless you are traveling w a big group, it’s not worth it.