has he ever tried to cross the border to Canada before? I saw many Americans who were crossing the border by land were never asked for proof of ties to the US.
But, most Americans have less reason to stay permanently in Canada than he does. The following quotation from elsewhere on the Internet sums things up:
If you are applying for a visitor visa you MUST show proof that you WILL GO HOME. You must show proof that you have a job, that you DO have bills to pay, that you DO own or rent your own house/apartment, that you do have family still in your home country and that you do have a return airplane ticket leaving Canada.
U.S. citizens don't need a visa, but they must meet the same general criteria. If you're coming for a short vacation, and you claim to have a job and a home to return to, there will rarely be any problem. His problem is that he has no job, no house or apartment of his own, and no money to spend on an extended period of tourism in Canada. He does have family back in the U.S. but it's his father who he hasn't lived with for 7 years and that's balanced somewhat by the fact that I'm family that he has in Canada.
The border guards need to be sure that he intends to return after his tourist time is over and that he will not work illegally in Canada. That's their job. They will tend to be suspicious in his case.
He's been to Canada twice. The first time, in 2008, he flew to New York state and I went and picked him up at the airport and drove back across the border with him. He didn't fly to Canada because he didn't have a passport at the time and it wasn't needed at the time, either. We were taken aside and questioned for several at least half an hour and two agents went and took everything out of my car plus checked under the seats, etc. He was out of work at the time, which they didn't like, but he was due to return to start a job re-training course, plus he had a jury duty request that he had to get back for. So, finally, after about an hour at the customs and immigration building, we were on our way.
It probably helped that he did have a return flight booked, too, though from a different airport.
His second trip to Canada was for U.S. Thanksgiving in November 2009 and this time he flew to the Ottawa airport with his passport of course, as they are now mandatory. First of all, he got in trouble for bringing sweet potatoes for our Thanksgiving dinner because root vegetables are prohibited. They took him aside and questioned him thoroughly about why he was coming and who he was staying with, how we met, how long we had known each other, and whether we were in a relationship. He finally admitted that we are. They can just stamp the passport (or even not stamp it) and there is an implied 6 months, but for whatever reason, the IO decided to only give him 4 months.
He did return after 5 days, just as he said he would, and he was able to show an Internet return flight booking printout at the time when he was admitted. (His return flight was from a U.S. airport because that was much cheaper.)
So, he's in a worse situation than he was either of those times, and both times were hassles. Yes, he could some for a short tourist trip (maybe 2 months, maybe 6 months, I don't know). But a short trip, while better than nothing, is not really what we want. And coming temporarily while already intending to extend it later might just get us in trouble. I was reading about another way to do things, but I'll have to write about that later, because I'm out of time right now.