Indiana is the coldest, windiest, iciest state in the USA. Flat. Pure miserable.
That said, Your summers arent even close to our winters. Dont think my dau said it got below 65-70* last winter. My oregano grows abt 18" above ground level in a raised bed that gets rain only. Too wet in the sandy area for growing in ground. It loves to cuddle up next to a cement block, or stone, and drape and creep itself all over.
Your conditions are so very different. Treat it like a basil tho- wait til creepers are maybe 5" long before you snip the xtra length back. Good luck!