While there are a variety of factors that influence reseeding, it doesn't take long to get a feel for how it acts in your area. In my area, I used to double crop buckwheat when bringing an old logging deck on-line as a food plot in the spring/summer and plant winter rye in the fall. It worked but I found better practices over time. Double cropping buckwheat gave me a lethargic first crop because I had to plant early enough to get in a second crop and the soil temps were lower than I would like. It also required 3 plantings a year. For some reason, I need to do at least light tillage when planting buckwheat on my soils.
Over time, I learned it was better to start in the fall with a mix of WR and Crimson Clover. Both surface broadcast pretty well if I don't want to do the light tillage. All of these crops are good soil builders. However, I found that if I start in the fall, crimson clover reseeds and grows in the spring. I can mow the WR to release it or just let it head out depending on the relative thickness. WR is not used much by deer in the spring but the crimson clover is. It is also providing N. I can then wait for soil temps to get close to 80 degrees before planting a single crop of buckwheat.
This method has the advantage of reduced tillage (good for the soil), less work, less expensive, and does not "clean the table" for deer. One key to this is understanding what kind of reseeding to expect from the crimson. This technique may not work as well in an area where reseeding is poor.
Thanks,
Jack