I have a couple questions about winter wheat. When is the best time to plant and what is an approximate price for seed? I'm looking to plant 10 acres.

We usually start planting around labor day but it really depends on the ground moisture. If its super dry its not going to grow whether you plant now or in November. Check your soil conditions and get a little fertilizer if needed. That can make your price go from very low to high real quick so your costs are going to depend on your budget and to what level you want to farm your food plot.
Good luck. Be sure to take before and after pics.

Any idea on price? Do you buy it by the pound or by the 50 lb bag?

Certified seed is sold in 50lb bag. Regular cleaned seed is sold by the bushel (60 lb). You do not need certified seed.

Haven't got a price yet for this year, and some reports indicate a possible significant price increase due to the drought (less seed available). Usually, you are looking around $8 to $12 per 50 pound bag. Just call around to several feed stores in your area to get current pricing. If broadcasting (rather than drilling), you will want to plant at a rate of 100# to 140# per acre. Like others said, planting time will depend on available moisture. The first of September would be the earliest date, but you would be well advised to wait until some rainfall has hit your area, and more is in the forecast soon after planting.

I think you can expect to pay $20 or so per 50 lbs for whole(non-certified) oats this year but I don't know what the cost for wheat will be but I think the price will be up from last year.

I just bought a bag from our local seed supplier. It was $19.50 a bag(50 lb), up from $11.00 last year.

Unless we get some real rains at my place, I dont plan on planting anything this fall. There is not enough moisture in the soil to germinate the seeds.....

I planted last week and I paid $11/bag for wheat and $12/bag for oats. I hope this chance for rain we have this weekend pans out. We had about an inch at our place back on 8/12-13ish.