I paid $260 for my orange Courier and $200 for my red Courier and I don't regret it. The red one is in pristine condition with buttery soft leather and the orange one has a story behind it. It's 2am and I'm awake worrying about work again so I'll go ahead and tell you that story while I try to keep my anxiety quiet, lol.
I watched that orange Courier on eBay for a very long time, maybe a year. It was priced at $175. This bag was a Holy Grail for me but I wasn't comfortable paying that much for a bag at the time. It got to the point where every time I bought a different bag I thought that the money I spent on each different bag was money that could have gone toward that orange Courier. Well, one weekend I was scheduled to work overtime on Saturday and Sunday, so I decided I was going to go ahead and use my OT money to buy the bag. On Sunday (maybe Saturday? I can't remember) I was taking my lunch break at work and I was in the process of completing the purchase for the orange Courier but I stopped myself, thinking what happens if I have to go home early and don't get my full 2 days of OT pay? So I backed out of the purchase and decided I would wait until Sunday afternoon, after I had worked both days.
When I got home on Sunday, I went to purchase the Courier but the seller had ended the listing! I wanted to cry!! At some point I got on TPF and started whining about how I missed out on it. Then it was re-listed but it was an auction this time, not a BIN, so I had to place a bid. I don't believe in bidding wars so I always bid at the last minute. Even if I have to go hide in the bathroom at work or set an alarm for the middle of the night. The day this auction ended was also the day I bought those 19 vintage bags from the estate sale for $150. I remember that as I was driving out to buy those bags I was thinking that I don't really want them, I want the Courier, and I shouldn't be spending $150 on bags I don't want. But then I thought that I could practice my rehabbing techniques on them and sell them for enough to pay for the Courier. When I got home from buying those bags, I bid on the orange Courier even though there was still an hour or so left of the auction. I then spent time sorting out the estate sale bags and when I knew that enough time had passed that the Courier auction was over, I sat down to pay for it but saw that I had been outbid!! That bag sat on ebay for a year and no one bought it, so it never occurred to me that I would get outbid! What a nasty surprise. So now I was sad and angry because I missed out on it again and now I was stuck with 19 bags I never wanted, which I mostly bought to sell to earn enough money to buy the Courier. (Flawed logic, I know. The courier was only $25 more than the estate sale bags, so I was nearly doubling what I was spending instead of just buying the Courier.)
As time went by, I missed out on 2 or 3 more orange Couriers because I got outbid again or I was worried about the condition of the bag. I think one had evidence of mold, so I passed on it. Then one day, (insert dramatic music here) lo and behold, my rust orange Courier pops up on eBay again! Not just any rust Courier, THE rust Courier. The original rust Courier that had started my obsession. By this time I had learned who the original seller was so I contacted them and asked if it was really the same bag. It was! So I negotiated with the current seller but I could only get her down to $260 from her posted price of $289. This irritated me because I knew what she paid for the bag, she had outbid me months before! In the end, I decided to go for it. I bought it. I love it. I don't regret it. But I learned something. From now on, when a HG bag comes along and the price is within reach and somewhat reasonable, I will go for it! And, if you ever find a bunch of authentic vintage bags at an estate sale, buy them too! Because rehabbing is fun and I ended up getting my money back for those bags plus enough to cover the cost of the Courier. It all worked out in the end.
I would have bought that Sherbourne too if I hadn't been told that I will either be laid off or begin working reduced hours soon. That bag is a unicorn IMO, especially in British tan. We're not likely to see another one any time soon.
Sorry for the long story! It's now 3am and I have 30 more minutes until my alarm goes off for work but I feel better having spent the last hour watching Harry Potter while I type out this story and then re-read it a thousand times to find all the stupid auto-corrections and spelling mistakes my tablet makes. It kept my mind off of worrying about work anyway.