We've got several areas that were cut last year and we're trying to make the most of the open areas. Would it be a bad idea to plant sawtooth oaks or other mast producing trees among the pine stumps?

Assuming you own this property, it depends on what is being done with the clear cut areas. Are they being replanted? If so, with what? Do you have the ability to keep the area clear?

We do not own the property but we are making adjustments to our lease to utilize areas that we take out of production. So, yes we will be able to keep the area clear.

I’m not making any long term investments to a property I do not own. I know too many people that have had leases yanked out from under them.

I agree. But when you say "out of production" what do you mean? Are you paying the owner to take the area out of production?

Loosing the lease is always a risk but I am talking about putting a few trees in the ground not dumping thousands of dollars into the property.

It is a timber operation and we don't have many big plots. Yes, if we clear one acre of trees for a new food plot then that acre has been taken out of production.

Are you talking about planting oaks in the rows of pines they have thinned? If so, I doubt the timber company would be happy with that. They thin those pines to eliminate competition for the remaining pines. Also, the oaks would grow for a few years but eventually be stunted once the pines enclose the canopy again. If you are referring to the loading decks left from a thinning, I would convert those into food plots as opposed to planting oaks that will take years to get any results from.

You provide more food properly maintaining natural forage mechanically, chemically, or with fire.

Oaks are a long term investment. I would not waste my time doing that on land that I lease and don't own. I agree with Nighthunter, fire and fertilizing natural forage is your best best, along with supplemental feeding.

This, but I would add that even planted food plots can provide a great deal of forage if done right.

I wouldn't think it would be a bad idea. Its all a gamble on losing property or changing locations but 5 or 10 years down the road you end up in the same place you will think. Dang sure wish ida planted them trees.
And not like you can go burn a piece of leased property

Is the land owned by a REIT? If so, then there is no way I would waste my time and money as they change hands with the weather.

I planted several pear, apple and crabapple varieties on my place about 12 years ago. They're producing pretty well now, but I get a LOT more coyote, possum, and coon action around them than deer. A few deer come to them, but the deer prefer weedy browse a lot more.

I am with others in saying that you are better off maintaining natural forage.

Pick a few areas of thinned pines, especially if they did 3rd or 5th row thinning and you have lanes that extend through the area.
Keep them mowed to about 18" high with a bushhog and add time release fertilizer. Even better, add some lime and then fertilize!
There are many places to buy native perennial seeds like partridge pea and aeschynomene that can be established if desired, also.