Some years ago I had to clear some towering (30-40') oaks for a new leeching field. At the time oak lumber was $6 per board ft. (1" x 1" x 12"); I had $$ in my eyes until a friend said "there isn't an oak tree in New England that doesn't have ants." Sure enough, they all had ants, and I ended up burning them for firewood.
Not knowing your specific lot and trees, I have to generalize. With the exception of a few straight, former "field" trees all the oaks on my land and most of the oaks I see in the woods and formerly wooded sub-divsions in MA are curved and appear distressed if not unhealthy. You might want to consult with an arborist (horticulturist) as to which (if any) of your trees should be removed first and site your garden accordingly. For removal, a tree service (whack 'em & hack 'em) would probably be cheaper than an arborist and could be contracted for stump removal. It takes me over a day to limb, buck, chip the slash, and haul the logs to the woodpile (leaving the stump to rot) when I have a 16" oak blow down. When I had tree service remove a 24" cherry between my house and the power lines that I did not have the courage to tackle myself, they were on site for 2 hours with a crane, chipper, skid steer and two trucks plus 6 men and a detail cop.
From my perspective with 1.1 acres you would be better (and more quickly) served by hiring out the large, capital intensive equipment tasks and leaving yourself with a SCUT or even 2-wheeled tractor for yard work.
Your generalizations are pretty spot on. Two of the trees I need to take out are completely dead - quite sure it's ants, and in the past, at least 50% of what's been cut has had ants right up the middle. I'm definitely under no illusion that there's any kind of $ in those trees.
I took out a couple of large oaks myself during the summer. Took me two weekends (but that also included the bar seizing up on the chainsaw, and cutting into a nail in one of them - both of which required trips out to fix).
Of all the work around here that should be done - this is the job I'd like to have someone else do, but ugh the cost is something else for so many trees.