Craftsman tools commonly sell for more than Proto, and it has probably always been that way. There's a lot more brand recognition there, so the listings will get more views and there will usually be more people bidding for Craftsman items, which helps drive up the final price. Proto is also one of the cheapest US made tool brands to source new, so that holds the used prices down noticeably compared to some other brands. Challenger is Proto's budget brand, so by default they will fetch less money than Proto.
Your tools should all sell okay, but in general the larger a lot is the less money you will get for each item. You have to balance lot size with shipping costs to find a happy medium zone. If the items in the lot don't go together somewhat you will also get less for it. Some of your lots seem like groupings of pretty random tools, whether they all have the same brand stamped on them or not. Sometimes having trade specific tools grouped together works out better than having brands grouped together. Also, you would probably be better off changing your auction duration to 7 days or less. Very few people are willing to wait 10 days to know if they are going to win an auction or not. Longer auction durations can work out well when you are trying to sell a very rare or sought after item and you want as many people to notice the listing as possible. In a situation like that, people will often be forced to wait the 10 days because there might not be any other way to get the item. For more common items, people aren't usually interested in waiting that long so they buy from someone else instead even if it costs them a couple dollars more. For instance, I usually find what I am looking for at a good to great price after keeping an eye out for a couple days max, so I often completely ignore auctions that have more than 2-3 days left on them. By the time longer auctions end, I am usually already done making my purchase, it is almost at my door, and I have moved onto something else.