Do you think he would have been a car mechanic? Since we have seen numerous times he's been under the bonnet of 'Baby' or inside kicking out any dents that may have serviced on a hunt. It would also bring them in some cash from time to time, he could even do it between hunts, do a Bobby Singer and have his own yard outside the Bunker?
Any thoughts ......
Jensen said a couple of conventions ago that if Dean wasn't a monster hunter he would be hunting the ladies.
I don't think he would have a yard. He would own several high end, luxury sports cars dealerships.
Dean likes the finer things in life and while educated Dean wouldn't be a marketing executive à la "It's a Terrible Life", he would still market the hell out of his skills and become the guy collectors come to for rare, incredible cars and to take care of their very expensive toys.
Dean is wicked smart. He has the soul of a hustler and knows how to charm people, negotiate and earn their trust. He's also a born leader, and he'd be making Dean all over the country and travelling with a briefcase full of hundred dollar bills and cigars. My story and I'm sticking to it lol.
I think all the way through Season 5 that Dean thought he could have been a mechanic, but in a pipe dream kind of way. It's what he was in WIaSNB. It's what John was before Mary died. John is probably the one who taught him almost everything he knows about fixing 'Baby,' and what John didn't teach him, I think Bobby probably did (body work etc. that Dean knows how to do to fix her every time she gets totaled). Even in Bad Boys, we see that if he couldn't be a rock star, he wanted to be a mechanic. He loves cars, and likes figuring out the puzzles to fix them.
Then in season 6, we see he actually worked construction, and Baby ended up under a tarp. As long as he was a hunter and couldn't do it, I think he would have considered being a mechanic, 'living the dream,' but when forced out of hunting (He still looked for Sam and cases in his neighborhood, but he was trying to fulfill his promise to Sam), it kind of tarnished the dream and is something that would've reminded him too much of his life. Basically, the dream was so intertwined with hunting that he couldn't do it and not be reminded of hunting, Sam, and being the last man standing in his family. Besides, there's no way he would have let himself be truly happy with Sam in the cage with Lucifer and Michael for all eternity.
So, I think if there were no more monsters, spirits, angels, demons, and Sam was alive and well, that Dean might be able to let himself have his pipe dream, but at the same time, I don't think being a mechanic would be enough for him. Remember that the first thing he ever wanted to be was a firefighter. Saving people is something that he was born needing to do, and he also needs something that is dangerous/high intensity, which is why hunting is perfect for him. He'd probably still need something along those lines to make him want to get out of bed in the morning. If he'd never had to become a hunter, I think it's more likely that he would have done something like that and fixed cars on the weekends as something of a hobby.
Something that gives him pure joy nowadays is cooking, and it's something he came to all on his own. It's not something anyone taught him, and he always looks so happy when he comes up with something that works in the kitchen. When he had the Mark and summoned Death, he made taquitos and tamales. It was an offering, something he knew Death would probably like, but when Dean's offered Death things like that in the past, he's given him the best. For instance, when he gave Death fried pickle chips, he gave him the best ones in the state. Dean making the taquitos and tamales himself ensured they were of a high quality, but it was also the most personal thing he could do. It's the only thing he could offer that was was all him, and it was all him minus the hunting (In other words, not weapons, not Baby, etc). So, maybe he could've been a chef and volunteer firefighter if he'd never been a hunter.