About 9 years ago, while finishing a Mastering Delphi book, I decided to spend three months in San Francisco, doing the copy editing work and the like by commuting to my publisher's office once a week. This ended up as a very nice experience, but that's another story. Knowing that you are allowed only 90 days in the US under the visa waiver program, I booked a return flight 90 days after my outbound one. This was indeed a mistake. The visa waiver program is for 90 days including the day or arrival and departure, that is 89 nights. Having realized the problem I did ask several people at the Italian consulate and elsewhere how big a deal this would have been. "Not a big deal", everyone told me. And inded no one complained when I left the country and a had just a couple of extra questions when I got back a few months later.
Fast forward to year 2002 (or 2003, I'm not even sure). I take another trip to the US (there have been a few in between, even after 9/11) and I get questioned, send to second level inspection, questioned even more... was threatened refusal to enter the country, but was allowed under a special provision (possibly because I was with my wife and daughter... but probably because I looked sincere. They asked me things like: "how many trips did you make to the US over the last 10 years?". Now, many people will know, but I was getting in and out about 3 times a year at the time, so getting the exact answer was tough. After some thinking I was guess an answer, and the police officer would correct me, as he had the exact number on his computer. "How many days on average?" this went or for half an hour. Now, beside my answers and my family, what really saved the day and got me in the country that day was that I had a US taxpayer number, related with the writing activity. I didn't realize at first, but I'm sure this made a big difference.
I was allowed in the country, but this was the end of my trips under the visa waiver program. Get a full visa, I was told. And I did. After spending 100 USD to apply, getting a document from my bank saying I was a known and reliable person, making a couple of trips to the US consulate in Milan (line before entering, take your number and wait, get to talk with someone don't really caring about you), I ended up with my 10-years business visa. I cannot stay more than 180 days each year, but can do as many trips as I like (apparently). Now, this is done I though, foolishly.
Since that time, in fact, and until 7 years from the original accident had passed (there is a 7-years relevance for some offenses, I've been told) every single time I went though customs I was told: "you're record says you need a full visa to enter, I see you have it, but you I don't have the power to clear you, so you need to go to 2nd level inspection". At this further inspection I generally get even fewer questions, as I do have the visa I need to have. Having dared to ask why, I was told this is the proper procedure, no way to change it. Now, if my questioning at the 2nd level is generally a couple of minutes, it can take an hour or two waiting before you get to that. I had once to wait for a Romanian lady to get her daughter enter the restricted area from the outside (she was waiting for her mom at the airport) after they tried for about half an hour to make her translate questions and answers over the phone.
Over the last few trips I was once spared this hassle, than had to do it again... so I'm not sure about the future. I know I have to allow for a lot of time before connecting flights! And I'm not sure what will happen once my current password expires (as this would happen while the visa is still valid). The good think is I don't need to get the new "electronic" passport, which is now required to enter the US under the visa waiver program, as I do have a regular visa.
OK, this is the story. Is all this making the US more secure? I really doubt. No one ever checked my criminal record (not that I have one!), but my bank and taxes. Is this preventing people obtaining illegal jobs in the US? Possibly, but I'm not really sure if this works. I could just keep saying I'm traveling for business for my Italian company, and none would object, nor check I'm actually paying taxes (all it matters is formally have a tax payer number!). Right now entering the US for tourism or for business is harder than in any other country I've been to (well, with the exception of Singapore, where they asked me to see my slides two weeks in advance and I had to be "cleared" on the actual content of my talk). As most measures are more formal than substantial (like the fingerprint stuff you have to do every time you enter or exit, the electronic passport, the terrorist lists with so many errors....) I wonder if the hassle is worth. I really doubt, but in todays world, you certainly have to live with it.
And one last thing, never ever pay for your flight with a check when it gets printed a couple of days before living (I had booked it over a month before at a local travel agency), because it is very terrorist-like to book a flight at the last minute paying cash! Oh boy, how many times I was questioned on that trip a few years back... what saved me that time was the booking printed well in advance.