Your friend is right from what I've heard. Top-roping anything is a good idea if you have a rope-gun. I wouldn't even think about leading for at least a season.
meh- with that logic if you are going for Rainier and are a reasonable person you should bivy. That is pretty subjective in my opinion. Some people don't like to bivy. I'm one of em.
Edlinger- Are you speaking to over-bolted routes? Personally I find climbing on over-bolted routes is easy and stress-free. Not that I personally advocate over-bolting. All that is to say Condomorphine Addiction is a good solid route.
I have a little beta on Serpentine. Did it late to mid June last year. Brought crampons and ice ax, only used to ax to chop steps on the approach. By the time we got to the top it was glissade conditions. I'd bring one or the other.
I went to Seattle Hand for a non-climbing injury for a follow-up to remove stitches. They were great. The real credit goes to Swedish Ballard for stitching it though.