While I don't disagree, I won't go so far as to say I agree. My Dad owned an outboard repair business for a number of years when I was growing up, and I spent my summers as a kid changing water pumps, changing gear case oil, and helping rebuild engines.
I know what good lower unit oil looks, smells, feels, and yes even tastes like. After a season of heavy use, even if the lower unit didn't leak one drop of water, the oil still has a different smell and feel to it. I don't know why, but something in it (probably an anti-corrosion additive or something like that) most certainly breaks down with use.
After a season of heavy use, it's still oil, and it's still lubricating, but it's not quite the same as what you put in originally. I don't know what is changing to say if it is really less effective or not, but I do know this.... My first car was paid for by people not checking and changing their lower unit oil often enough.
Good old black dead-dinosaur and prehistoric-fern-based 90 wt Hypoid oil certainly has a unique smell. I won't argue that!
Mine is not a blind recommendation from a consumer, but rather it is based on extensive outboard maintenance knowledge as a hobbyist vintage motor mechanic. I can tell you off the top of my head that it takes a 9/16 wrench and a 7/16 wrench to drop an older OMC lower unit,
after looosening the fine-thread bolts under the shift shaft cover with a 3/8 wrench...

But that's not important right now.....
I do know today's lubricants are significantly better than they were "back in the day". My 50's era outboard motors were designed to be mixed 24:1 with 30WT automotive oil. Today we use TCW3 as a better lower-carbon-fouling substitute, (still 24:1, I don't like rebuilding power heads and oils is relatively cheap). Many LU lubes are now synthetic, and are certainly multi-season. I would suspect that a 2008 Honda probably has synthetic in it. just a hunch, I have not searched it yet.
I have to consider your comment in context. Your example points to a season of heavy use. My little vintage runabout's '57 Johnson got drained and refilled every year, because I used it a lot. I mean like every weekend for several years until I finally put it in the shop and covered it up. On that point, you and I are on the totally same page.
Considering the light duty asked of an outboard sailboat auxiliary though, I have no problem at all recommending that LU lube can go two or more seasons, assuming the motor has not been punished, there is no excess of wear metal, and the lube is dry and the same color as when it was first put in. If it has browned or darkened appreciably, as that is a visual clue that there is a need to change it.
I highly recommend routine and proper maintenance. It is a good habit, and breeds other good habits. I just want to stop short of making a statement that can be perceived as a scare tactic that causes someone who is not as familiar with a topic to fear for the worse...