Speaking of cars, by modern standards, they were death traps.
I already lived in the 1950s. I’d go back if I could bring my Thai wife. Could always pass her off as a Japanese war bride. Then I’d head straight to Vegas and be a betting fool. Presidential outcomes, certain celebrity deaths, war outcomes. I’d be the wealthiest man in the world in no time.
Oh, and in the suitcase, I’d bring selected books that I would then proceed to “write” myself. For example, if I could go back early enough, say 1950 or the beginning of 1951, I could submit Catcher in the Rye for publication. Just let that poser Salinger prove I knicked it off of him! Might have to bump him off first just to avoid any trouble. Thank goodness there’s no DNA technology. Say, maybe I could “discover” DNA while I’m at it!
I think I would have to learn to become a good liar. I’m in my mid 50s and if you dropped
me off in the year 1952 I would have pass myself off as some born in the late 1890’s.
Sooner or later someone is going to ask what I did during the war (World War Two ended
just 7 years ago) or how I managed to support myself during the depression. When discussing
the music I listened to when I was young it might be better to mention Al Jolson or Helen Kane
rather than Elton John or Queen.
It seems to me that it would be a bit inconvenient living in the fifties. No ATMs and the banks
are only open from 10am - 3pm on weekdays. My car would need it’s oil changed much more frequently
than an early 21st century car and would need a tune-up every 10,000 miles or so. And until I
made my fortune investing in stocks that I know are going to go up in price I would probably
be working in an office were several of my coworkers would be smoking.
For a particular personal reason of mine, I’d be in seventh heaven if I were on the receiving end of this deal. I’m British, not American; am a railway and steam locomotive enthusiast, old enough to have known steam in plenty in everyday commercial service on my own country’s railways. All I know about steam on North America’s railroads, informs me that it was magnificent, but ceased (save for a few anomalies) to run in normal service in both the USA and Canada, as at 1960.
I’m aged 65, in good health and with a pretty strong constitution. I presume that under the arrangement, I would be retired, with an adequate retirement income from whatever source. I’d dedicate my new life in America, for however long I lived – armed with what knowledge I now have, of how things developed through the 1950s re North America’s railroads and their steam locos – to seeing everything I could, of the rail scene. Would follow steam wherever it lasted, and would do maximum possible travelling on passenger trains – whatever the motive power – while that possibility was widespread (before long, rail passenger services in the USA would diminish most drastically). I’d use my house in the suburbs as a base, but would essentially be an itinerant, roaming the rail system as widely as possible.
After the end in 1960 of significant US and Canadian steam; this type of motive power continued in action in Mexico until the late 1960s, and in Central America for a few years after that. I’d see turning my attention to those parts, post-1960 – with possibly some visits for steam to other continents, funds permitting. At probable best, I would be getting too old and decrepit to travel, about the time when “steam north of Panama” mostly faded out.
I’d thus say, “please, Mr. Rob, come and call in on me with your amazing offer – and is there any chance that you could ‘bump it up’ for me, to a few years before 1952?”
Those of you talking about bringing back sports results won’t have it so good. First, the casinos doing legal sports betting will get to know your face very quickly, and in the 50s the guys running casinos weren’t so nice; and second, you’d have to spend time finding a local bookie and then you’d piss him off very quickly. I suppose you could establish a network of runners in Vegas, but that wouldn’t last long either.
Stocks work, however, especially if you have weekly or monthly valuations. You wouldn’t even have to wait for the big winners like Microsoft - you could just identify small, fast winners.
I could do pretty well in my current field, but I’d probably go the stock market route and go back to trying to write short stories, at a time when my odds might have been better. The tricky part would be trying not to borrow snippets from stories I already know.
You’d only need one win at exceptional odds to be set for life. Just bet on the winning team at the very beginning of the season, put everything you can on them. They’ll gladly take your money, because it would be so farfetched that you could be right so early on. Then what are they going to do, break your legs because you named the winning team?
You would have been too late. She started modeling in 1945 and by 1949 had been spotted by the movie execs in the Groucho Marx film “Love Happy”. Perhaps a young Rachel Welch would do as runner up. 
Just curious, how old are you?
ETA: And OP, why ROB?
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If the idea is to bring back one aspect of modern knowledge to 1952, then I would bring the scores of every pop song written by Lennon/McCartney, Gamble&Huff, Holland-Dozier-Holland, etc, and use the copyrights royalties from my songwriting acumen to fund my stock market wizardry. 
I would definitely stay away from gambling*. It’s illegal, and the stock market isn’t. Win too much while gambling, you’re likely to get hurt/killed/investigated. Win too much in the stock market and you’ll be rewarded/admired/investigated. I know which outcome I prefer.
*Except, perhaps, for a certain Super Bowl in 1969…
The day Roger Clemons was born?
Just shy of 50.
Horse racing is the way to go here. Legal gambling available in a many states. Just the Triple Crown races would give you three big payoffs each year. But even then you’d want to go with just one big year to get yourself rolling. After that you’d go to Vegas and mix in some losses to throw off bad attention betting on other sports while you waited for stocks to pay off.
Can it be the one where the waitress are on roller skates?
Yeah…playing chicken is no fun when the cars have airbag, anti-lock brakes and collision sensors.
It’s not illegal in Las Vegas. And they can investigate me all they want if I make a bet there in 1953 that John Fitgerald Kennedy will be elected president in 1960. Imagine the odds I could get at that date. Why would they anyway? And if they did, I’m sure the OP’s got me covered as far as my back history if the authorities go snooping around.
It’s not the authorities I’m worried about, it’s the criminals. Some book has to pay you $50g in 1952 money and you think you’re just going to get paid, go to “Vegas” and gamble on the future, in a city run by the Mafia, with no consequences?
Better to become Warren Buffet. Safer and easier too: the crooks all carry briefcases, not guns. 
They couldn’t come up with a scenario in which I managed to rig the 1960 national election in those intervening years.
Dude, it’s the Mafia, not the Justice Department. Even if they completely and absolutely believe that you just made a random and extremely lucky bet, that’s still not going to stop them from deciding a bullet in the back of your head is cheaper than paying out on your long-shot wager.
You’d have to get there ahead of me. Although I didn’t mention Salinger in my post - I can see it now: “Catcher In The Rye…by Siam Sam? Hehe - looks like I’m not alone” 
Good points. If you’re betting in an illegal venue or in a legal venue where there are likely to be mob connections (formal or informal), you want to look like a lucky bastard, not a wizard, or, worse yet, a cheater. Maybe go to the track, lose a few times, get to know some people, become a regular, win a little, then make a few more losing bets, then win big.
Did they have any State Lotteries back then? Seems that the government would be less likely to, uhh, go after someone who won Pick 6 than mobsters would be likely to go after someone who won their racket.