For a cruise, I've done the night before and the morning of (very early). I'd prefer the night before just to be safe (not to mention the morning flight was a pain because it was so early!)

I did do a repositioning-type flight last year on award in which making the second connection was critical. I debated flying out a day early, but it made no financial sense since that would mean extra 2 room cost for our traveling party.

We finally decided to fly the day of and I buffered 6 hours or so of extra time. I'd rather hang out at the airport than miss the international segment that took me so long to set up. Figured 6ish hours of buffer time should do it. I'd have to miss about 3 domestic connecting flight to totally miss my target and figured that the trip is not meant to be if that happened.

Our first flight ended up getting moved earlier by 3 hours, so we ended up with like 8+ hours at the airport.

It was a long wait, but nothing that the lounge and a proper meal at a restaurant couldn't fix. We were tired by the time we got onboard and we were all able to catch some sleep after the onboard dinner.

My layover for a LHR -ATH was also roughly 7hrs. Sure, a bit of an overkill but it sure beats being rushed!