Regarding insurance, some photographers that I know use Hill & Usher to insure their gear. Or you might try Safeware.com.

Personally, I travel regularly and often take photographs in what some would consider sketchy places (Yemen, Kosovo, ...). One (soon two) DSLR camera(s) always come along for the ride. To be less obvious that I have cameras, I carry the cameras in a large messanger bag that I have converted into a camera bag. Of course, for me, I often have a tripod and usually have the camera in my hand, so, uh, yeah, that's hard to hide.

Theft of the equipment is always a worry, but I find that the best thing to do is use you common sense, be aware of your surroundings and keep your equipment attached to you or your chair as much as possible.

Backing up your photos as often as possible is also very advisable. The equipment can be replaced, the images can't. I suggest backing up images on a portable harddrive (or your iPod), or burning CDs as you go and when possible uploading your favorite shots to flikr or what ever web storage service you prefer.

How did you convert your messenger bag into a camera bag? I tried that but I couldn't find any padded inserts. Instead I got a crumpler bag which is a camera bag but it doesn't like like one - the whole point of it. The problem with that bag is that there's only a enough room for the body and twin lens - I could squeeze a few small things like a my point and shoot camera, sunglasses, but not much else.

The crumperbag is a good option. But since I frequently carry around a tripod (yeah, defeating the stealth of a camera bag that doesn't look like a camera bag), I don't find the Crumpler products convenient. There is not a good place to hang the tripod.

My original messenger bag / camera bag had leather straps that were sewn into the top of the bag and fastened to the bottom. I could lash my tripod to the straps for easy access. Sadly, that bag finally died. My new one has a slip pocket through which I slide my tripod. It is still convenient, but not as.

To answer you question: I foud a padded camera waist pack that fits one SLR and three lenses or two SLRs and two lenses. It also has a zipper pocket for small items such as spare batteries and memory cards. The waist pack slides easily into a large messenger bag with room for another lens case or other accessories. The messenger bag has additional pockets that I use for batteries, cleaning supplies, memory cards, shutter cable release, notebook and other items. It also has a secure inside pocket for valuables (i.e. keys, passport). The added benefit is that if I really, need the extra room, maybe to carry home a couple bottles of wine, I can take the waist bag out and use the messenger bag.

Incidently, I am designing a new messenger bag to my specs that I will have made here in Cairo. I'll send pics when it gets to the prototype stage.

Finally, Thinktankphoto offers a pretty nice line called Urban Disguise. My only problem with them is the tripod issue.

Lovetravelling - Not sure if it is just different insurance companies/difference in country of origin but I'd check your fine print in your policy.

The Luggage limits in the policy that I have is:

$3500 - Camera and Video
$3000 - Portable Computers
$500 - Other Items

This policy also allows me to increase the limits of any particular item I choose (at extra cost of course).

Trekker - Take your camera. If you spend your entire life worried about the 'what if's' you will never travel, you will never go out your front door. Go, take your camera, have fun. After all you could leave your camera behind and while you are away some low life breaks into your place and steals your camera...

If it is going to happen it will.... no matter where you are. So go out and live!