Mini hp pump in the jersey pocket, in another pocket alway a bit of food on 2h or longer rides, road is wired when you are going, it seems that I need to eat at 2hrs and than I can go for another 2. Banana or Nutella sandwich is my go to food. Fuck powerbars and that stuff unless racing or really training specifically, it seems to me to be wasted money.
Saddle bag, yep unless racing.
Tube, patches, levers, multi tool with chain tool, bottle opener,and co2. I carry a spare co2 for friends and enemies that get flats(i get them from work, if you are buying co2. Just get a nice full size zefal pump.)
Lights, even clip on blinkys are great for when it gets low light and you are out drinking.
http://www.mec.ca/product/5013-171/capsul-case-wallet/?f=10[HTML_REMOVED]q=Case I bought one of these for a wallet and it is perfect, cards a couple bills and go. Phone in a ziplock bag as well.
Fitted jerseys are awesome, loose is pretty cheesy and doesn't wick well, tight is only really important if you want to save watts on your TT time, but srsly you will look like an over stuffed sausage. At least I do.
Spd's: you don't need any clop clop skittery roadie super patent leather shoes. They will give you a small amount of power transfer improvement, but if I poop before a race I get the same improvement in w/kg. the first time you buy beer and fall on the slick floor you will hate road shoes. I race once a week in crabon soled spuds and so do many of my teammates, they are faster than me and also value the walk ability of SPD's.
Don't waste money on super light tires, they flat too easy. Look for affordable excellence like Gatorskins or Duranos. You can do the odd gravel path and not freak out because you will not get flats as easy.
Road is ok, just different than MTB. I love it for leg speed and training. The distance you can cover in 5 hours is amazing.