I think the wolfman will be fine, seen them come up from from a funky back pack maker in Colorado USA where you had to look hard to find anyone who sold them to what there are now selling world wide. I do not have any of there dry bags but there bags are first rate. I have a back pack from them that is 25 years old and have had there tank bag in my hands it looks like will last a good long time. Still do not have it as it is a toss up with the packsafe and my tank bag I have now still is ok. Thing is with dry bags is once some one cuts, burns, or rubs a hole in it it is not a dry bag. So you may want to take some small bags, stuff sacks, or compression bags (do not compress as they use more space when there round than when there not) to keep things in that must stay dry well dry, it will also help organizing all your stuff. There have been people ride the world with them and still use them.

I have a givi top box it is ok but do not like for long trips I like a box with a tall sides and a short lid still can not find a good reason to replace what I have as it works. Have seen people make it RTW with a givi on the back and love them. Also seen people make it with givi side box as well seen others hate them and end up dumping them and take soft boxes or have hard boxes made on the way. Seen people do the same with TT boxs on the side as well. Any thing on the bike is at risk.

One thing you may want to look in to is packsafe net for your bags Pacsafe Anti-Theft Bags & Travel Security Products
helps with people using a blade to cut open your bag.

That camera set up looks grate Do not know if the 50mm f1.4 will get you any thing more than the cheaper 50mm f1.8 also the little 18 to 55 vr focus is vary close and can be used like a macro (micro in Nikon talk) also you can get a close up lens some times called diopters looks like a filter. shoot raw and jpeg fine the cards are cheap and small take lots. Do not think "is this going to make a nice shot?" shot first then think how can I make the shot better. One thing about the kit 18 to 50 and the 18 to 200 is there not as well made as the 50mm. But then I am a old film shooter and like the old lenses than are steal. Next time I take my 50 to 200vr I need to make a holder for it or it may not make it back.