It's been my experience with cycling clothing that you get what you pay for. I started with the cheap Performance stuff and worked my way up and so far, everything has been well worth the extra cash. I haven't gotten to the Rapha/Assos level yet; Hincapie/Castelli/high-end Pearl Izumi have kept me satisfied thus far.
Waterproof and windproof mean that if I'm riding hard it'll get too hot in a hurry. Windproof tights were too binding on the knees and not necessary for my 30's F riding limit. I don't need to commute by bicycle in the rain so I've not focused on waterproof though I have some waterproof(actually water resistant) jackets that are useful at the start of rides until I get warmed up or if I'm stopped long enough to cool down.
I think it's better to have a lightweight water proof or resistant shell and wear that over your winter jersey or jacket than to have one jacket that does both. That would probably end up being too warm to wear for very long unless you are riding slowly(as with grandma).
I prefer layers. One can always remove a windbreaker and ball it up and shove it in a pocket.