Oregon, huh. You are a rarity on this forum.

A small garden tractor would really help to pull a large drag all over the yard. The drag is what will do all the leveling for you. What kind of grass do you have? If you have a broad mix of grassy grasses and broadleaf plants (aka, weeds), I'd be inclined to not spray anything first. It could be your weeds form a majority of the plant material.

Most of the grasses growing in the PNW are not the type that spread. If you have any of the following, bermuda, Kentucky bluegrass, or bentgrass, then those will spread. Bermuda is usually a warm season grass but you might be close enough to the Pacific and far enough away from the Pacific to keep it happy enough. If you have rye (very popular in the PNW or fescue, then it is not going to spread all by itself. If you seed it now and get a hot summer, all the new grass will be stressed and may die. So there's that consideration.

Before you start you will need a drag. A hand pulled drag looks like a 6-foot wide by 4-foot long piece of chain link fence attached to a 6-foot long 2x4. Attach each end of a 12-foot rope to each end of the board. When you drag that thing behind you over the loose sand, the drag will knock off the high points and deposit the loose sand into the low spots. Drag it every which way to get it as level as you can. If you rent a lawn tractor you can make the drag much bigger and go much faster. If you want to do micro leveling, drag a piece of fabric like a rug behind you. Doesn't matter which side is up.

Here's how I would go about this.

1. Move all the dog toys away.
2. Fertilize.
3. Water deeply (as you always should).
4. Rent a mower and lower it all the way to the bottom setting. Mow and remow to get it low. Remove all the clippings.
5. Take delivery of several pallets of bagged masonry sand. With bags you can return what you don't use.
6. You and several of your husky friends spread the sand out.
7. Use the drag to level.
8. Water lightly to settle the sand and let it dry a little. New low spots will appear.
9. Repeat steps 6-8. You might need to let the sand dry a little before dragging.
10. Celebrate with beer and pizza for your husky friends. Do NOT release the beer before the job is finished and YOU are walking away from it. They will continue to help you if you hold the beer and pizza as final payment.

Water it daily for 2 weeks unless you get rain. It is already fertilized, so water is all it needs. Mow when the grass is tall enough to mow. I'd keep the dog toys off the playing field until you are sure the grass is knitting in. It will be the roots of the grass that hold everything in place.

The initial length of grass will be a factor in the amount of sand you need. If the grass was 5 inches high, you'd never be able to level it because the grass would be in the way of the drag. If it is 1/4 inch high, you can level it to a pretty fine degree.

1 cubic yard of sand will add 1/4 inch to 1,000 square feet. If your yard is 5,000 square feet, you'll need 5 cubic yards to raise it 1/4 inch. Moving all that sand around is why you need the husky friends.

Thanks for the great advice. I've attached two photos of the grass, so not sure if this helps. It's about 30% grass, 30% clover, and 30% broad leafed leaves. I'm okay with the clover, but would like to phase out the weeds. I think I will just spot spray the nasty ones (with stickers), and deal with the others over time.

Freshly mowed:
{{gwi:94320}}

Not freshly mowed:
{{gwi:94323}}

I do have a riding lawnmower (that is older than me, but it runs...) to use for pulling a drag. Since I have plenty of places I can use the sand for other projects and due to the cost in this area, I will go with the dump truck load of sand and rent a tractor to spread the majority of it. (I need to get the tractor to add in some new fencing for my horse pasture anyways...) Than I can make the drag you described below and drag and drag and drag. I do have an old carpet piece I can use also, so depending on how long the day is will add that part in.

Keep in mind, that even with a hot summer, when I was putting in fence posts about 30' away from the bottom of this field at the end of June, I hit water at 16" below ground level. Hence why I never have to water my lawn. There are some patchy areas without any plant material that I think I will add some grass seed, and will baby this summer, with the expectation that I will need to resand and reseed next spring.

Thank you for the ordered to do list - it's very helpful. I will report back how it goes! The only "husky" friends will be my mother and I. We may have also added an additional project to the list of moving a 24x24 3 sided shed and having a bonfire, ha, so wish us luck. At that point, we'll skip the beer and head straight to the margarita bucket!

One last question - is there a good way to tell when the grass is "knitting in?"

Thanks again!

Make sure you go SEE the sand before you buy it to make sure it is consistent and a clean medium course sand (mason quality). Many sands have small pebbles and/or sharp slivers of stonein it. If the purpose of sanding is to soften the ground, I would suggest that you aerate well before sanding. It is one of the reasons that golf courses aerate and sand, to soften the greens so the green absorbs some of the ball's impact and redoce the bounce. It also helps in drainage.

Good points by grass1950 on sand selection. I have been burned by sand before. It was not the sand I had selected.

Grass is knitting in when the new roots are holding it down.