printing picture of some one! car on tee shirt

wfll said:

If I were to have a website where people uploaded pictures of their car, motorcycle, boat, etc., would I be at risk of trademark infringement by printing the shirt?

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If people were only uploading images of cars that they owned and you were only printing one-offs for their personal use, you should be ok.

But if they don't own the cars or you were printing dozens or hundreds for them to sell, you could start having issues.

wfll said:

What if I have a trademarked tagline that printed on the shirt with their picture of the car, etc?

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Taglines are trademarked for the purpose of giving the trademark owner the exclusive right to use it. Using it without license or permission would be infringement.