FWIW, a couple years ago I saved seed from supermarket acorn and the resulting plants were fabulous and gave great fruit. Shoulda saved more seed from them but I didn't. This past Spring I had a whole bunch of volunteer acorn and butternut in my compost pit, so I transplanted them in the veggie plot. The plants grew beautifully, putting out flower after flower -- ALL MALE. So I waited...and waited...and waited...and I finally said after a couple of months the heck with this and pulled those suckers. It was an all-boys club, no girls allowed.

Your friend should have tons of little oak tree seedlings in his yard from the oak tree. I have oak, maple, black walnut, paw paw and tulip poplar seedlings all over my garden. And I have lots of squirrels who get most all of the acorns, but they must miss a few. LOL

cweste, Good advice so far. If you're looking to do a significant reforestation featuring oaks - and hickories! - planting 'locally-adapted' strains of species native to your area is your best bet. Direct seeding of locally-gathered acorns, or transplanting 1-2 yr seedlings of those local-sourced nuts - or from your state forestry nursery - will likely meet with better success than purchasing from a forestry nursery in, say, PA or IA, or soliciting acorns/nuts from folks here who are in very different climate/growing conditions. I'm all for growing 'specimen' trees, usually of 'natives' that either aren't 'native' or, at least, common, in my area; but if I were doing a true reforestation project, I'd want materials from a relatively local source. From your description of the site, some pecans(yes, I know it's a hickory) and black walnuts would also be in order - though with the looming potential debacle of Thousand Cankers Disease, you might need to consider J.microcarpa instead of J.nigra.

I have several acorns on my Chestnut oaks, I have 2 Chestnut oak trees, they have put out acorns after just about 3 years in ground, maybe even 2 years, they grow hella fast, and NOW I am getting acorns on my Swamp White oaks, they may be about 7-8 years in ground from whips about 2 years old, SO Swamp white oaks will give you acorns in POSSIBLY about 8 years from planting til fruiting. and I also am getting small acorns from my Pin oaks and my Nutall's oaks and 1 Shumard oak tree. I am still waiting to see my Compton;s oak trees acorns, I do KNOW they will be rather big acorns, at least compared to most of the acorns from the PIn oaks, Nuttall's oaks and Shumard oaks, it seems like most white oak acorns are larger than the white oak acorns. Anyway, I hope that the original poster could come here and respond to all of these answers, it would help to see if my reply and all of these other replies have helped to answer the OP's question.