64 Times the Harvesting: Let's Play Harvest Moon 64

[Deme]

There are 2 events that you work, right? The second one is the one that permanently destroys some of the stumps IIRC, so on the days you work you should chop wood during the evenings. It's harder to get wood after that. I'd say work all 5 days, though you might need to make yourself have fewer morning chores.
.

You forget the magic of The Dog Race, where you can exchange medals (of which we have a lot) for 500 lumber. We can, even before the fall horse and dog race's winnings, afford 1000 lumber. It's why I'm not in any rush to get lumber; we can get a lot of it for very little work, enough to pretty much last us the rest of the game.

...However, if you guys are interested in us getting the Greenhouse faster than mid/late Winter, we can work on lumber more in the evenings.

But yeah, there are two events.