Will OSB be okay during Wisconsin winters?

I wouldn't do it. I don't think it would last 5 years. But then again, I'm not convinced that plywood would last 5 years either without some sort of treatment. It might not fall apart like the OSB will (it comes unglued), but it will warp and pull up at the seams.

If you're on a budget, then why use something that you KNOW isn't going to last and you'll have to pay good money to replace? Doesn't that just make it twice as expensive? It seems like saving pennies but wasting dollars.

I think that your OSB with a primer and EXTERIOR paint coat could last 5 years. Don't let it sit directly on the ground. Mistinted paint at Home Depot only costs $5 and would be a good investment in $ and time.
 

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