this is what i do for outdoor crops.
find spots a year in advance and be sure to check where the sun is (it changes position) your gunna want it to be hitting your plant more directly towards august-october. see how much in the area stays green towards the end of september/beginning of october. a big plant can stick out like a sore thumb.
i start my seeds in starter trays, these are my first round for this year(white widow regs), i will start seeds when i have room for them all the way till mid june. they start going outside in the beginning of may and should all be transplanted planted by mid july. they will stay in the seed starter tray for at least two weeks, i'll pull all the crappy lookin ones and the rest then go into solo cups for two weeks. i personally prefer to give my plants at least a four week head start before they go outside.
i plant in clearings in the woods, corn fields and along the edges of soybean fields. when planting in fields it's best to wait till mid june to put those plants in the ground. most farmers use seeds genetically altered to resist round-up and will spray there fields at least once after there crop is established. (here where i plant they only spray once).
your gunna want morning light over evening light to help prevent mould on your plants. if your using a tree line you want a nice east to west clearing where your plants can get about 8 hours of direct light, the more light the better, it will help them finish faster and yield more.
i take out one 1.5 cubic foot bag of ocean forest per 3 plants, i'll mix it with existing dirt, if the area is sandy bring more and be ready to have to fertalize during flower. i get alot of run off in my spots in the woods from the fields in my area and i really only fertilize a few times per season.
skunks possums and raccoons will dig up your plants, the smell of the dirt makes them curious, i sometimes use chicken wire staked down on the ground around my plants to prevent this. but prefer just pile up larger rocks (10lbs or more) around your stalks, this way you don't have to clean up as much at the end of your grow and they will be there for next year (i do move them).
i pee around my plants a lot and also take human hair (my sister cuts hair) and spread it around, we have a lot of deer here but i have never had a plant eaten.
i always have problems with four lined plant bugs (pic of the bug) in may and june. they will leave brown or black dots on your leaves, making it look like it's from a disease. it usually takes 2-3 applications of insecticidal soap to get rid of them completely, but once there gone they seem to stay gone for me. when spraying for bugs be sure to get under your leaves too.
i try not to check my plants more than once every couple of weeks but when there's problems like bugs checking everyday is crucial.