I am planning to visit a friend who lives in Palo Alto Nov 17-24 and will be staying at his place for the duration. I am planning to also head into SF on most of those days and am debating over taking the Caltrain Vs renting a car and driving in (my friend does not have a car). The Caltrain appears to cost $14 / day for a total of $98 if I were to go every day. I can also rent a car for the duration of my stay for $140 total (pickup and dropoff at SFO). I am also probably going to get a SF CityPass which includes a 7 day Muni pass.
a) take Caltrain from Palo Alto into SF and ride muni
b) drive from Palo Alto into SF and park where there is free parking and ride muni to wherever I need to go if necessary
I like the driving option b/c it allows for flexibility in timing and I can potentially drive right up to certain places (if parking is free). It also allows me to easily visit places (perhaps even not within SF core, like areas surrounding Palo Alto), that are harder to access via transit. The car also provides storage of purchases while in SF. My friend may also join me in SF on a couple of the days so the car is nice as we both save on Caltrain fees.
So the question is how is SF in terms of free roadside parking? If it exists, are there usually ample spaces? Any good examples if any? Ideally, I'd like to drive as close as possible into SF such that I can park somewhere for free for the day and access the Muni easily from wherever I park. I am willing to pay a bit extra for a car rental due to it being much more flexible and convenient, but if finding somewhere to park for the day for free that is within easy reach of the Muni is a huge problem, then that convenience goes out the window.
Oh and I guess free parking may not be absolutely necessary, but unless parking for the day ends up < $5 or so, it will get to the point where I'd rather just go with the Caltrain option.