I'm definitely in the camp of "if it's raining, I'm getting wet." I hate riding in a rain jacket. I have a fancy gore-tex "breathable" just for bike riding jacket, and I still hate wearing it. I still end up pretty much soaked eventually, if I ride for long enough and if it's raining hard enough, plus sweating like crazy in the jacket. So I pretty much just go out with a soft shell if it's chilly, and my normal riding clothes. If I'm commuting to work, I have dry clothes/shoes in my waterproof backpack/panniers, and I just towel off and change at work. Stuff newspaper in my shoes, and if you've got a little space heater at your desk, they can get pretty dry in a work day! I used to freak out about riding in the rain ( I live in CO, it doesn't rain much here!) but one Spring it rained every day for about 45 days...it was either stay inside, or get used to the rain. It was cold, rainy, and my shoes were literally wet for the entire 2 months, but I learned to enjoy it and basically stopped wearing any waterproof gear because I got sick of feeling like I was riding in a trash bag all the time. (I also train/race bikes, so I was riding a ton.)
Oh, also, Lots of companies are making super cheap, flexible plastic fenders that zip tie/velcro onto forks and seatposts...these are great to catch a lot of the annoying spray that gets glasses/butts wet in super wet conditions. I even had a friend make one out of one of those cheap flexy plastic cutting boards for $2.00!
On the bike maintenance point, clean/dry your chain every night if it's wet outside. Apply chain lube ( I love Dumonde Tech) and then in the morning before riding, wipe it off with a towel. Super easy.