I will do my best to answer these, some are based on my personal experience, i.e. I have witnessed and addressed the issue personally on at least one occasion, and some will be based on my opinion, i.e. although I haven't witnessed it personally I think I may know the thought process...
1 & 2. Our CC Agents are for the most part younger and straight out of college. They are basically, and please don't mistake my use of this term, our first line of defense when answering routine questions and accomplishing the daily tasks that are needed. I have overheard, which i can't help since all 20-25 of them sit literally right behind me, some of the CCAs give out erroneous information. When this occurs I do my best to figure out what is going on and make sure they have the right answer. I do not believe that they do this with malicious intent or with intent to mislead any of our customers, it is just not every question has the exact same answer. There are several areas that need to be looked at and considered when trying to diagnose exactly what is either causing an issue (such as what you experience yesterday) and what options may or may not be available. In most call centers, the CCAs are given a standard FAQ to follow and for the most part it covers 95% of the questions they will get in a day. Due to the nature of this type of business, not everything is cookie cutter or black and white, there is a heck of a lot of grey to wade through to get the right answers. Basically they are doing their best with the limited knowledge and experience they have. Is that a good answer, No, it isn't, however just like in the military you go to war with who you have, not who you want.
My best advice is persistence without belligerence. The minute you start blowing up on these kids, most of them will shut down and not be inclined to go too far out of the way to assist you. If you feel that red curtain starting to drop, take a breath, ask again and at that point if you still are not getting the answer you need ask to speak with a manager, you can drop my name if you wish and that may put the proverbial foot to butt and get their CC Supervisor on the phone. Understand, there are only 2 supervisors so if they transfer you expect to wait a while before they answer. Your best bet is to ask to have their supervisor call you back. Once again, if you don't receive one within a reasonable time frame, let me know.
In regards to your specific issue yesterday, I am not afraid to say that I don't know. I sent it to the Tech Support Lead, he fixed it. I asked if this issue was widespread, he said No (literally that was the only two letters on his return email). This is the reason why I need to know if other individuals have been effected by a similar issue. It was most likely just a "ghost in the machine" fluke which happens quite often. If one letter/number/space is added or deleted "over the air" or during a download it wrecks havoc on the entire issue. This is one of the disadvantages of being an online company, technology "glitches" every now and again and no one knows why. If I can show that it is a systemic issue, then I can stand on the Tech Geeks desk and validate the reason I need them to research the underlying issue. Unfortunately there are too many tasks and not enough fingers on keyboards to fix every single one-off, so they will prioritize issues based on what and how many people/items are impacted.
Once again, your issue yesterday is a glaring example of the above. I or the auction management team should have been notified about this one. I would love to know who exactly you talked to yesterday (you can pm me so we don't put them on public blast) so that I can conduct a little corrective training on what needs to be elevated immediately. Within seconds of looking at the screen shot you sent I knew what was "wrong with that picture" and immediately sent it to TS to fix. That should have happened yesterday, and as you say the trailer would be sitting in your collection and not on the other side of you neighboring state. As far as waiting, yes that is perfectly acceptable. You made the attempt in good faith, and you will not be penalized for not picking it up. The only time late pickups become an issue is when there is no attempt to schedule or no one bothers to answer the multiple emails that are sent out (day 8, day 30, day 45, day 60) before the actual abandonment date.