I don't think it's been talked about much; but I think it's somewhat worth mentioning: What kind of life has Dante been living up until DmC? I was replaying the demo and noticed what I had first thought was Dante's gloves clipping through his jacket; but then realized it was just the jacket itself has some of the red pattern on the arms worn off. It made me think; exactly how has this Dante been living?
Looking at the jacket itself... it's not in good shape. It's very wrinkled; worn and faded. Brand new a leather coat like Dante's would cost a small fortune; but looking at Dante's, he's either had it a long time or simply didn't get it new. Looking more in-depth at Dante; we know he's had a messed up childhood and spent a lot of it in an orphanage; in juvenile detention centres; and probably a good bit of it alone after he escaped. He's been chased by demons his whole life so it's unlikely he ever had a chance to get any sort of education; not to mention he's also a wanted criminal so normal jobs are out of the picture too. And there's no Devil May Cry so it seems unlikely people are paying for him to hunt.
Looking at all that; it's kind of impressive that he even has a trailer to live in.
I think the stuff with him being labled a terrorist only happens when the game starts. He gets blamed for the incident at the carnival after the Demon Hunter busted everything up, and if you remember Vergil's lines 'they're aware of you now Dante, so stay low' it could imply that. If he was still a wanted man before that isn't clear, but it could explain why he chose somewhere like the carnival to hide.
Part of that pier was like a trailer park. If he did have to pay rent it might only be with cash, so it removes the need for identification or any complications of paper work for paying bills or what not if you don't want to be tracked. Another thing is the carnival might be the last place anyone might consider looking for him
(demons included) but at the same time keeps him in near the city so he can still go clubbing and have fun without feeling cut off from the rest of the world
(Because if Dante really wanted to disappear completely, he could've just jumped on a train to somewhere rural and lived out his days in the country, although he doesn't exactly strike me as one for the quiet life).
If Dante's stolen or robbed, it's possible. Likely it's something he'd of done a lot in his teens to survive and he might pickpocket every now and again from the rich sort that could afford losing cash if he got desperate. But I think if Dante does have a job before the game's events, then it might very well be at the carnival he's stayng at, for the same reasons of living in the trailer; to go undetected.
As for being poor, by the way he dresses you're right. Dante probably only has enough cash to get by on, same going for clothes. His jacket shows wear and his shirts looks old like it's been washed a bunch of times and has lost its whiteness. Nothing on him looks new, but you could also tie it to Dante just not being great at cleaning his laundry. If he hasn't got a washing machine, he'd probably just take a bag of dirty clothes and dump them all in one machine at a laundromats/launderettes without bothering to separate the darks from the bright ones.
Meanwhile anything he has in his trailer is probably stuff that he's accumulated up over the years, like the combichrist poster
(not just being a reference, but a band he might like) and an arcade machine he could've gotten at the carnvival if it was being tossed out for being dated. Also if you look, you can just see a computer screen in the far back. It's nothing modern, so it's likely second hand or what was going to be thrown out. There's sentimental items too, like the the statue of the angel with the neon lights. Dante has a thing for angels, no question from how he behaves around the angel dancers in the club, but it's probably behind his amnesia/memory issues on not remembering his mother well or that she was an angel. It would explain why he would have something like that in his trailer and also explain his angel fetish for women dressed as them.
Put together, all of this would imply Dante's lived in that trailer for at least a few years. He's gotten settled, but is still scrapping together what he can to survive; keep food in his stomach and the clothes on his back. He's coping, but he has it tough. He's lost without a purpose and lives each day like it might be his last because he never knows when the demons will seek him out and finish him for good. So, the idea of starting a demon hunting business probably hasn't popped into Dante's head, not as of yet. I get the feeling something like that might spring to mind during the course of the game or near the end. With Dante going and taking out these big boss demons for Vergil, it could get him into that way of thinking of
"hey, maybe I can do this for a living".
I wouldn't be surprised if by the end Dante did get his little business started up, since by then sociality might be aware of the existence of demons. Remember, we did see the city getting torn apart and innocent people getting hurt, so it's possible.