>>602424I can give you advice based on my personal tastes (25,000+ km of touring) but I've met quite a few people who successfully tour while doing things differently from me.
-Rain pants are useful if it's cold and wet. If it's only wet or only cold, they're not worthwhile. If they aren't designed for cycling, make sure you can keep the right ankle from getting caught in your chain.
-Deciding between the hammock and the tent depends on where you're going. I tour with a tent because I've found myself camping in places without trees on a number of occasions (pic related).
-I find a bear bag pointless. Keep all your foodstuffs in one pannier and hang that pannier in a tree. A bear bag is designed such that you can keep your food in it without making your backpack smell appealing.
-Unlike
>>603669 I have no problem keeping track of my stuff while touring. A place for everything and everything in it's place. Bringing stuff you don't mind losing can't hurt of course.
-I do food differently than you plan to. Buying just-add-water dinners, peanut butter + tortillas for lunch and just-add-water cereal for breakfast is cheap, light and low-volume. I'm type 1 diabetic, so being able to eat anywhere and any time probably much more important for me than you, but I appreciate not needing to worry about when and where I want to eat.
-Keeping stuff in your pockets, wearing a watch or a pack is obnoxious while cycling. Put it in your panniers.
-You can get a pair of cycling shorts pretty cheap and they make a big difference. If you're worried about looking too FABULOUS with skin-tight clothing, you can find semi-baggy shorts with chamois inside. It makes a big difference over hours/days/weeks/months.
As far as distance goes, 500km shouldn't be too hard to start off with, even without much training. I'd expect to clear it in 4 full cycling days. Most other tourers I've talked to would do it in 5.
