I've read the posts so far and don't see anything positive re: Oakland so let me try while staying very objective. I grew up in Menlo Park so I am familiar with Redwood City as it was then -- and my family still lives in Menlo Park with my dad's office now in Redwood City. I also lived in Los Altos as an adult while working in Silicon Valley. And I've lived in SF, moving to the Montclair district of Oakland (one of the really nice areas) when I got married.
*Commute: This is a toss-up depending on mode of transportation and where you are going. Driving from the Peninsula to SF is easier than driving from Oakland *but* taking public transportation to the city from Oakland (BART) is easier than from RWC (Caltrain) -- I've commuted via car, train / BART to SF from both locations for work. Also, getting into the city for evening events (dinner, symphony, baseball) seems to be easier from Oakland ... you tend to feel closer to the city and the city's culture in Oakland than in RWC. I often take BART, meet my husband who drives into work and then we drive back together. Driving to football games at Candlestick is easier from the Peninsula than from Oakland.
*Shopping: This is toss-up in my mind contrary to other posts. RWC is close to Stanford Shopping Center which has all of the best shops but you still need to drive -- an easy 15 - 20 minute drive and free parking lot. From Oakland, you can get into SF for shopping more quickly than from the Peninsula if you are going on a weekend day for example. However, I generally shop in Walnut Creek -- also a 15 minute drive -- which has almost all of the same shops minus some of the very high-end ones (Nieman Marcus, Lord & Taylor, for example) plus some really cute boutiques. There are free parking lots and paid parking.
*Poverty / Crime: You are right on Oakland having higher crime rates. RWC used to have high rates as well, not sure about today, I believe it is better than Oakland now. RWC has gone through some "gentrification" in the last couple of decades as the cost of Bay Area housing has gone up. It definitely had a low-income population when I was growing up but lots more families have moved in I think. Occasionally you do drive through the tougher parts of Oakland to get to places you are going ... not that often but it does happen.
Anyway, I hope this helps!