I usually till in two or three passes, depending on how hard the soil is. If it is rocky, I do the first pass going forward, with the tiller rotated backward, so that it is spraying some dirt forward. The rocks get tossed forward and are easy to collect and remove. I do the second pass in reverse, with the tiller rotated all the way toward me, and as deep as possible. If it goes to full depth, I'm done. If not, I do a third pass at full depth in reverse (no tire tracks).
If it has been dry, I will bet that you will be happier if you water it enough to dampen the soil to depth.
I also mow/mulch ground cover first- less gets would up in the tiller and it composts faster. I sharpen the tines occasionally to help with tilling roots and ground cover, but it doesn't make a big difference for me.
All the best,
Peter