It would do both with just one “groundhog year” pill. Live a year with my current wealth and use the experience of that year to plan out how to earn money when it repeats. At the same time I would use that first year to measure my health so that I could take precautions or act on all that accumulated knowledge when the year repeats. There would still be a second pill to choose, and I think I’d choose the +3 charm because I could also really use it.

But I don’t think this would work how I envisioned because I misunderstood the “groundhog” pill. I think it’s supposed to mean that you repeat the same day 365 times, which wouldn’t work for lottery/investing. So then I agree, taking the $π million and +3 charm is probably the best.