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| Personally I don't bother with the waterproof stuff since let's face it, if you're on a bike in the rain you will probably get wet, as long as you have enough clothes on and you're working at it on the bike you'll be warm enough. I wouldn't worry about getting wet but keeping warm is important.
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I asked my husband about it, and he said that if you take care of your waterproof gear, it does work, but at the same time, if your haveing a good ride, your gonna get wet anyways from the sweat. if you use a backpack, i would suggest that you get a rain jacket for it, it seems to work longer with keeping the rain out.
and etc, dont worry, just make a list of what you want, then prioritise what is most important and so on... it will help with not feeling overwhelmed with the costs. Dont go to Manor and buy it all 75 percent off and get stuff taht will only last 3 months, try to get good quality. Go to any big name sports shop and ask questions before buying. Oh, and if you have problems with getting your pants dirty on the bike chain, consider a "hosenband". It helps keep the pants from rubbing against it.
Good luck