Have contacted Stripe to see what they might suggest as subscription schedules wouldn't be ideal for you since it'd collect a partial payment, run for the overflowed days, then collect the remaining payment and go for the full year. We're only using subscription schedules for actual differently configured initial payments and durations where it makes sense.

I might have a possible solution using free trials though since the bonus time is a free trial and they're not paying for it. Specifically the "Bonus time before first period start (for calendar-based durations)" and "Bonus time when reactivating expired subscriptions" parameters are what is causing this issue as they're pushing the subscription duration over the 365 limit.

There isn't a solution for this at this time. Your plan is outside the limits of Stripe recurring payments. Stripe didn't have any solutions to offer unfortunately. What I could come up with is basically hacky workarounds to try and hide the free trial or multiple subscription stages. For example one is to use a free trial to offset the extra days, but make the first billing free and charge the initial amount as a one time fee, but there's risks to this going wrong and it's not really intended to be used this way.

For now it seams Stripe just isn't going to be able to be a solution with your current plan structure as they've a very limited 1 year duration for recurring payments. If this wasn't recurring payments then it wouldn't matter what your duration was so you might need to consider not using recurring payments and have them renew manually to use Stripe or consider using 1 year duration instead of by calendar year.