bjjoondo 

A lot of the "options" are just what "YOU" decide you want to carry. For me the #1 is buy and wear "padded bicycle shorts", as your distance increases, you will THANK yourself that you bought them, jmho. They have MANY very cheap "headlights" that put out a decent light these days, make sure you get "LED" and not Halogon, the LED's are truely better, (Check out Cat Eye.com for lights). Since you have "trouble" with your hands, look into "GEL" riding gloves and they even have, GEL bar tape too, I use both, it helps. Getting your bike "Fitted" at a decent shop will go a long ways to getting your comfort level up from your old bike. BTW, as far as flats go, have the shop to put in, "Slime or Goo", it's like Fix-a-Flat for cars, also I've had REALLY great luck with tires that have a "Kevlar belt" under the tread. I'd still get a frame pump (recommend the Road Morph hand pump, it's got a bulit in gage and acts like a mini-version of a floor pump), tire patch kit, some plastic tire irons, flat tires, happen, no matter how far you ride, jmho. Yes, the Water Bottle and cage, I also really like my rear rack and rack bag combo, to put "stuff" in. YMMV.