TravelonHeritage,American,Classic,Modern

Q: Could it hold a dslr camera in addition to wallet, compact umbrella, phone, etc?

I don't see how a DSLR camera would fit in there but I may be wrong. The rest of the items, it depends on how large they are. this is a small purse but it does hold a surprisingly good amount! I have to wear glasses also but find they fit better if I slip them into the 2 pockets for them (facing the outer material lined wall) than to try to use the cases!

Q: Considering the shoulder strap appears to have a cable, does it ever become uncomfortable to wear?

The shoulder strap has no cable in it. And the bag is extremely small. It may measure larger on the outside but it is much smaller measurements on the inside.

Q: how long is the strap?

It is approximately 36" long as shown in the picture, but fully extended would almost be double that size. My wife said it designed to wear over your shoulder, as well as over your head. We are going to travel the Mediterranean this summer and my wife wanted something secure to put over my head. She got the information on the manufacturer site. Hope this helps.