Im not sure about how well Oak trees grow after you thin them, so you might wanna ask someone who might know more about Oak trees than a westerner..... that said, Buy a portable sawmill, make piles of oak sawdust and a few piles of oak lumber, sawn to grade can make you a tidy sum while clearing a few ttrees out at a time opening up the ground albeit a little bit. Logging is not wrong, just most folks never think about sustainable harvest of a timbercrop, and while 20 acres will not last long waiting for return growth, there is always a few trees to cut on your neighbors ground, hence a portable sawmill. Ive owned one since Feb 1986, and while it sits for months at a time, it was paid for in the first year i had it, cutting custom lumber at a measly .08 per board foot, price cost dictates most folks around cetral idaho now charge .15 to .20 per bdft which probably would vary from state to state placeto place..... anyhow, once you learn the value of a piece of oak furniture square you can saw for grade, and sell to custom furniture makers, even in small quantites if you have what they need at a reasonable price..... Anyone with timber can make it happen......and if you do it wron like anything else you could starve doing it as well.
I have a mobille demnsion circle mill, awesome machine for cutting any type of wood.... i have sawn side by side with bandsaws [woodmizer] and would have one if they gave it to me, but then again, even i could change if it worked better in hardwood than the softwoods we have here.
http://www.mobilemfg.com/ will get you started looking at what i am talking about, people often ask me hoe much i would sell my mill for, actually it is worth more to me than a new mill, as it is setup for sawing up to 28 feet in length, and becuse as a part wears out it is replaced , so basiclly it is a new mill that looks well used [built in 1977]. And it is awesome watching a log broke down into lumber, and every log is different and yet the same as well. The Almighty knew what he was doing when HE invented trees for lumbering.
William