Yes, start with 100. I'd personnaly consider doing the whole thing by hand if its fairly flat to begin with. If not, then start with 100 on a ROS to flatten it well, then go to hand, aagin with 100 then 150, 220. I assume since its a checker board you have opposing grain directions on the whole thing. If so, it might be best to do circular motion as opposed to with the grain on the hand work.
Keep in mind, the ROS will leave significant little scratches over the whole surface. You really need to sand these out by hand for a fine piece that gets so much up close hand touch like a board or a jeweler box, etc.
If you really want a nice feel you can go to 400 or even higher. I would. You can also dampen the piece pretty good with a sponge after the 150 to raise the grain. After it dries very well, hit it very lightly with the 150 again. Then go with an even lighter touch on the
220, etc. Once you raise and knock down the grain, too much sanding after that takes you down to the next level of fibers and you defeat the purpose.
Finally, apply some Tung Oil mixed with Turpentine (after you test the color). If you go to 400, it won't absord as quickly. You can use a lint free rag or 0000 steel wool. Be carful and use good steel wool because as it starts to degrade you'll get metal fibers that are hard to wipe away. After the oil dries for a few days you can use a good wax (I use Brie Wax). Apply just a little with steel wool in circular motion, let it dry and buff it to a dull sheen, or all the way up to a bright shine if that's what you want. Too much wax will allow it to mark up easily (finger smudges) so just use a bit.
All this being said, test the ENTIRE process on sample of the same wood first.