Does the engine come with oil already in it, and how do I check the oil level?

No — the engine is shipped without oil and must be filled before operating, as running it with insufficient oil can cause serious engine damage and void the warranty. To check the level, place the snow blower on a flat surface, remove and wipe the dipstick clean, reinsert it without screwing it in, then remove it again to read the level. Add oil slowly until it registers between the upper and lower level marks on the dipstick. (Page 8)

From the official Craftsman Snow Blower FAQs manual, page 8

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