Bare root seedlings ate absolutely the way to go. They will go in MUCH faster and in 5-10 years will be as big as containerized trees planted ththe same day.
But question 1) when was it last farmed? (In other words does it qualify for CRP - which will cover a % of planting costs, plus annual rental payments).
Question 2) does your state allow EQIP funds to be used for tree planting?
(Can you tell I used to work for the government? LOL. Not that he has to use cost share...I've worked with plenty of people who didn't - but it can certainly drive down the cost to him!)
Regardless og that, I'd plan now for spring planting.
*Late fall, spray 18-24" wide bands with RoundUp. I recommend every 10'. Maybe 8', maybe 12'
*Order seedlings. 10'x10' spacing is 435 trees per acre. Order about 10% over because spacing is not likely to be perfect and you don't want to run out.
*Find a tree planter. Something like this:
kelcomaine.com
Several of the soil and water conservation districts around here rent them for like $25-50 per day so check around. Depending on how heavy the soil is 30-40 HP will pull it. Real heavy clay may take closer to 50.
*Find 3 people: driver, seedling planter, "stomper" to follow behind to step soil around seedlings and monitor depth (tell planter too high or low).
*Use a preemergent herbicide either just ahead of planting or as you plant.
We've planted thousands of seedlings per day doing this...
Option 2: use dibble bars or hoedads.
Option 3: Hire a migrant crew to plant for about $0.30-0.50 per seedling.
Next: weed control - either chemical (product will depend on what you plant and what weeds are causing problems) or mowing. Good preemergent reduces this expense drastically.
Finally, are deer going to be a problem? If so, you gotta stop them or all of the above was for nothing. Best 3 options:
8' tall fence
Peanutbutter fence
Individual tree shelters
This may cost more than the tree planting, but if you don't do it in a heavy deer area, the rest was a waste.