Let me try and take a stab at this.
What would He wear (jeans and t-shirt, suit, slacks with polo shirt, etc)? He would almost certainly not wear a suit. There is no indication in the Bible that he went around wearing fancy fabrics, or mutli-colored clothing, so we have no reason to believe he would wear fancy clothes. I have a feeling he would probably wear a t-shirt and jeans, though possibly some other type of pants, and something like a polo shirt or a semi-formal button down shirt.
What would He eat and drink (would He shop at the grocery stores to get products made in factories, processed food, etc)? Given that it is very expensive in almost any part of the country to by unprocessed foods, I have a strong feeling that the Lord would buy processed food, would probably have eaten at places like McDonald's, and wouldn't have bothered to spend the money to shop at a place like Trader Joe's.
How would He talk (with a certain style)? Well, he would speak English with the accent of wherever he grew up, just as he spoke Aramaic with a Palestinian accent, when he was here before. He wouldn't use foul language.
Would He go to college, go homeless, or just get a typical job (McDonalds, Walmart, etc)? He might go to college, given that the Bible shows he was well learned in the Torah, and college is the place that well learned people go. I doubt he would be homeless. I am not sure there is any indication he was such in the Bible, he seemed to stay at people's houses. Though, before he started his public ministry at roughly 30, he was a carpenter. I'd say that most likely he would get a trade like that as his career and would live in an average house, like he most likely did then.
How would He have acted in High School? He would have done his homework, respected his teachers, showed respect to all of the students, and probably joined clubs. He wouldn't have engaged in lewd talk though.
How would He view technology (computers, smartphones, video games, etc)? He would use them for good purposes, and stay away from pornography and probably from violent video games. He would have certainly had a cell phone, at least most likely, so that he could stay in contact with His mother better, and with His other loved ones.
What music would He listen to? Not Lady Gaga.
How would He view the Church? Well, it wouldn't exist. But if, somehow, it did, he would have been a member of it and viewed it as a good institution with flawed people in it, the Church not needing correction, but the people needing correction.
Would He get married? If so, what would He look for in a woman? He would not get married, He didn't before.
Since all American males are obligated to register for Selective Service, would He go into the service if He were drafted? I have a feeling He would be a concientious objector.
Would He watch movies or television? If so, what would He watch? He would probably watch the news, maybe American Idol (I hate that show personally though). He would stay away from things like Freddy Vs. Jason (probably), but would not likely be opposed to something like Cars.