Find flat spots, clearings, and old trails or roads, thats where I would look for coins etc. If I ran into a bunch of iron, I would spiral out from there, and get away from all the nails (where buildings probably were) and try and get in an area that produced a bit more than just iron and trolley parts.
Both sides of any roads "may" have had buildings, and I almost always find coins next to driveways, sidewalks, trails and roads in the woods.
Pull up aerial maps, you will be able to see paths, roads and clearings easier... take note of where large trees are and smaller trees are, that underbrush or smaller trees/ clearings will be an indicator that there wasnt patches of trees back THEN, as in trees less than 100 yrs old are probably new growth since the area fell under neglect....
Another thing if it were ME.... I would cherry pick high tones, looking for concentrations of coins, and not bother with low conductors... that is, until I got a better feel for what spots were hot and what weren't.
Run wide open, no disc until you get into a bunch of nails, then move away from where the structures were, you "should" be able to figure out where the hot spots are. Good luck!