I've been a lot more lazy with planting in HM: DS then in MFoMT. I've only planted 8, 9x9 squares and the season is almost two thirds over. I've been focusing more on befriending Daryll and digging up jewelry for Leia, finding harvest sprites and leveling my axe and hammer.
I normally start out clearing my home field of weeds, stones and branches. then I'll go clear most of the rest of the fields. Except on Mondays when I go dig in the excavation site for Leia's Tuesday gift. Tuesday I teleport to Daryll's house early in the morning and give him a grass to keep his friend points up, then go see Leia and give her a gift. Normally my cat, dog and horse get petted/brushed right when I wake up or right before I go to sleep. Casino visits and fishing are random, normally when I get distracted and forget what I had planned.
I think for this game I'll get Leia to a blue heart while working on getting sprites found and buildings built. Once I get the sprite for owning 10 (or is it 15?) chickens/ducks and the duck pond I'll start doing more in the way of crop planting.