user-experience fail
The last time I did this (a couple years ago, I think), I went to the USPS web site, chose my stamps, and supplied a credit card and shipping address. It took about three minutes.
Last night I went through the following process:
1. I dug through product pages; the generic "forever" stamps that almost everybody wants are no longer the first thing you see.
2. I also wanted some pretty stamps for some invitations, so I browsed those. Clicking on the link for a specific product to get a closer look and then going back to the previous page reset the page values I had set (specifically: show all, instead of in batches of twelve). So after the first time I launched new tabs to view products.
3. Some of these invitations are going to Canada so I had to look up the postage rate. This involved approximately the following, all in form-like interfaces: choose type of package, choose shape of envelope (kind of a stumper; is my card a "letter" or a "square envelope"? no sizes were given), choose weight, and finally get a price. I'd been hoping for a simple rate table or at least for the most-common question ("how much to send a letter?") to be answered up front.
4. Now that I had everything in my shopping cart I thought I was within a minute or so of being done. That "crash-tinkle" sound you heard was my hopes being shattered. My options at this point were to log in or create an account.
5. I tried the username and password that I would have used had I created an account last time and got told "no such user". (Bruce Schneier is cringing, I'm sure, but at least they saved me the trouble of trying different passwords.) There is still no option to just pay already. Ok, I'll create an account. (By the way, Firefox offered to remember that password I typed. This will be relevant later.)
6. The password-entry form includes an assessment of the strength of my password. Nice. It thus came as a total surprise to me that my strong password was also not a valid password. They said special characters were fine, but I guess they didn't mean all of them. I simplified to a less-strong password.
7. The personal-information page requires a phone number. I typed it with hyphens and it accepted that. It thus came as a surprise to me when, on a later page, I couldn't put spaces in my credit-card number. In neither case was there any direction about formatting.
8. I had failed to notice that giving my credit card a "nickname" (what? I'm only giving you one!) was a required step. Clearing all form fields and telling me to try again was unnecessarily rude.
9. I finally had an account and now had to log in. I wondered whether my shopping cart would still be intact after all this, but it was. Yay. 20+ minutes after I'd started, I was finally able to submit my order.
10. After signing out, I decided to sign back in and let Firefox remember some data this time, since I'd had to violate my password patterns and might not remember. The login dialogue wasn't the form that I'd previously encountered but, rather, some pop-up (Flash?) thing that was very sensitive (had to try a few times to get it). Firefox couldn't detect this as a login dialogue. So I guess when I come back in a couple years I'll be finding out what the "forgot password" link does. This won't be helped by the fact that I had to provide answers to security questions including the word "favorite". Pfft.
I liked it better when the minimalist approach worked. Yeah, sure, now they'll remember my address and credit-card number, but it takes me 30 seconds to type those and anyway the credit-card info will probably be stale by the next time I need stamps. I'd have to make an awful lot of transactions before last night's time sink would pay for itself.
Followup June 15: This is how they shipped my stamps to me. Those pieces of cardboard are pretty thick. I think they could have done better.

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FWIW, postage to Canada is, IIRC, 85c.
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rectangles and squares
Even if you write your address on a CIRCULAR envelope, figuring out which direction the lines go is a standard OCR problem.
Re: rectangles and squares
http://pe.usps.com/text/dmm100/tips-measure-letters.htm
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(That particular post office may be closed as part of UPS's cost-saving measures, however, and the next-closest post offices are both about a mile away.)
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I know of at least two 24-7 post offices - one in San Francisco (Rincon Center) and one in Los Angeles (near LAX). Most major cities have one or two designated major postal centers with long hours.
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You can, by the way, search upsps.com to find post offices open after 5 p.m. on weekdays or on Saturday or Sunday. Most Saturday hours are only 8 or 9 to noon, alas.
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