If ripstop nylon is the same as what I remember it to be "back in my day," it isn't expected to be waterproof at all. My backpacking sleeping bag was made of the stuff.

I've had waterproof garments wear out. Ones that I've used extensively for cycling wear out on the inside at the crotch and knees. The sprays don't completely restore the waterproofing, though maybe I could try a couple more coatings. Higher quality gear seems to last longer. It wouldn't shock me if super lightweight gear didn't last as long, but I don't know. Right now I have a rain jacket and pants from REI that have kept me dry for both cycling and hiking in pouring rain.

Thank everybody for the responses. It'll take me a while to parse all of the answers and pick something to buy. I apologize for not responding sooner, I was out of town.

Yes, I understand condensation, but during the day the majority of my rides are of the less than 5 miles sort and I don't tend to push it hard. I wasn't sweating on that particular day, and in fact, I rarely sweat unless it's >75 °F outside. (The downside to that is that I'm almost always cold unless it's >75 outside.)

And the condensation argument doesn't make a ton of sense. That would imply that the puffy (it was a "thin" puffy jacket) is breathable but the rain jacket wouldn't be. In my experience, that puffy is not breathable at all.

I'll try to spray some DWR on the jacket to see if that helps. Here in bozeman, we rarely get downpours (for more than an hour or so.) So I usually just have to deal with light consistent rain.

It's too bad the Arc'teryx jackets are so expensive, because it would be great if you could try one. I've never had something that works so well for so many conditions. It is not waterproof and doesn't even claim to be, but it's more comfortable than anything I've tried in the rain. I paid $100 for a Showers Pass rain jacket, which is on the low end of their price range, and I may not use it much any more now that I have the Arc'teryx jacket. The Arc'teryx is the only jacket I wore this winter in the coldest temperatures. With a couple of layers under it, I was not cold at all. I'm still wearing it on cool days, and it is not hot, either.

I really like my Storm Cobra hoodie from Chrome. It's got great ventilation, hood that fits over a helmet and does not leak anywhere. It's my "cool weather possibility of rain" jacket, for a real downpour I love my Grunden's Rain Cape.

Marc