I have one of these bags. Bought it at a carboot sale not knowing about the brand, for £10. It has seen solid use for 10 years with no defects. It's been around the world multiple times, all sorts of stupid heavy weights in it and no issues.

They have excellent customer service, so if they do chip or etc then they will send out a replacement without much questioning. I have done this multiple times, with handles which have fallen of mugs, to chipped or worn enamel.

Maybe. Are the laces tightened enough? Are your feet rubbing? Or is it the insole? In which case maybe a resole would fix that. I like my shoes to be a nice tight fit, and sometimes the laces stretch/leather stretches so a good tug never hurts.

They look perfect to me. Just the wray the leather warps to people's feet. I often busy hand made English shoes on ebay seconds hand in this condition. After about 10 hours they warp to my feet and fit like a glove.

Try Nudie Jeans. They do life time free repairs on there jeans. Super impressed by the quality. They can be bought for £20 online second hand or about £200 new. Highly recommend.