If travel is basically consuming the OP's entire day, an additional connection might be acceptable providing that it offers a good plan B for IROPs.

I agree that Saturday flights would give the best chances. Also, OP can pick RUCs for the DM choice benefit and use them to score a few upgrades.

It might be better to focus on the upgrade odds of various BUF-XXX and YYY-BUF shorter connecting flights and plan to sit in coach on the longer segments unless RUCs can be used.