I hear ya Maddog - I am in the same boat with a lot of my plots. I've got plots that are 'L' shaped, Pie shaped, No Shaped - LOL. I must have been a glutton for punishment when I layed them out. I am looking forward to see what others say here but I will give you what I generally do when I plant my plots.
This is probably the biggest headache. It is part of the "boomerang" shaped plot you see in the satellite map below. The back half of it leaves me a big pie shaped section once I plant the straightaway portion. Fortunately, I 've got that section in a 3 year alfalfa/clover rotation now so I only had to plant it once in 3 years. I use a Land Pride 606 NT pictured in my avatar.
The larger destination plots (3.5 acres each) I divide into 3 sections for crop rotation purposes (others at least 2 sections) so I am drilling about 1 acre of each planting. I generally will start in the middle and run lengthwise to the end of the field, pick up the drill and drive around to the outside edge and plant that in the opposite direction, pick up the drill and drive around the edge of the plot to the next strip just beyond the first one I drilled in the center, etc, etc, etc. I have these pretty well measured out so they generally come out even but sometimes I do have a little overlap on the last pass.
It looks like this:
The last pie shaped short section is a PITA, of course, but it is what it is when you plant small food plots vs large ag fields.
I have clover strips around the outside edge of all of my food plots. I do this not only to provide a clover component to my system (without planting other dedicated clover plots), but also because, generally speaking, annual crops don't always do well on the outside edges of plots where you have trees shading out the edges and also sucking up a lot of the moisture. Clover gets along fine in those conditions where other crops may not. It also gives me space to drive on when I am planting or otherwise moving around the property with the SXS.
Other fields like the boomerang shaped one that is split into 3 sections, I may end up planting up to another section on one end but it is usually a cover crop which is no big deal if I drive over it. Actually it doesn't usually hurt anything if you drive over part of what you just planted (as long as you pick up the drill) - maybe creates a little compaction but I really haven't noticed any issues with it.
On the ends of the fields, I will usually run perpendicular to the planted rows on the ends for usually 2 and sometimes 3 passes. If it overlaps some I don't worry about it. You can see where I did probably 3 passes across the end when I planted this cover crop...
This may not be the most efficient planting pattern but it works for me on my small plots.
It usually works out fairly well. The deer don't seem to mind if I have a little overlap here or there. If any of my friends or hunting buddies notice it and rattle my cage about it....well...they can just KMA!
