There are many factors that will indicate when the next pass is required. Mostly on what you are trying to do. If you are tying to turn the filed to absolute dirt, then several passes with a subsoiler only will be required. Here is what I do for turning a field into dirt if the only thing I had was a subsoiler. I'm assuming that the subsoiler is a multi-shank subsoiler with shovel heads like a chisel plow. To me, a subsoiler is thin stout ripper that is used for breaking the hard pan without really turning the soil. Many different terms get flung around for tillage equipment.
After the first pass, I wait until I see the vegetation that is left on the surface start to die. There needs to be some moisture in the soil for faster decomposition, but every time you turn the soil, you will loose moisture. Without rain or irrigation, this is the limit of time between passes. Another limiting time between passes is the vegetation coming back, or new vegetation that start to popup.
Once the vegetation starts to die, give it another pass at an angle to the first, this mixes the soil and keeps things from getting too rough. Keep doing this until the field is dirt. Depending on soil moisture, thickness of vegetation, etc, will determine how many passes/how long it will take between passes, etc. For me, I try not to hit the field first with a subsoiler/cultivator/chisel plow or what is known as secondary tillage.
Primary tillage, like plowing, tends to create a rough surface finish to the field. But does an amazing job of turning the soil to put the vegetation in direct contact with moist soil for complete decomposition. With plowing, you literally take the top 5-7 inches of top soil and turn it 180 degrees upside-down. Secondary tillage can be preformed very shortly after plowing. Secondary tillage is tillage that is used to create a finer, smoother surface finish ready for seeding, creating a seed bed. In my opinion, implements like a chisel plow, cultivator, etc are secondary tillage. But that is not to say that they do not do a good job of turning /mixing the soil, just not as efficiently as primary tillage equipment. I typically use secondary implements to smooth out the roughness (and to mix the left over vegetation into the ground if any) of a primary tillage operation.
I said before, that we would typically plow the fields every few years, that is not to say that we didn't turn the soil over every year. Typically after harvest of our row crop fields, we would simply drag a disk a few times over the field before winter. In the spring, hit it with a cultivator to loosen the crust and prep for seeding and whatever else we had to do. By spring, the majority of the previous years crop is dirt.
So time frames. Really depends. Just gotta do it, look at it, and do it again when you feel the time is right. If you all you need to do is prep a seed bed, run it over once or twice, pull some sort of leveling device like a drag harrow or cultipacker (to make it more smooth) and seed directly into the new seed bed along side to the existing vegetation that will begin to come back. Depends.
I noticed that the question asked was rather simple, and I responded with a wikipedia page. Probably not the response you were expecting, but I hope this clarifies some of the confusion for anyone. Tilling is a rather simple... complex operation that most farmers simply take for granted. You till the field, what's there to figure out? Well, for someone who doesn't know, there is quite a bit. And it all depends.