Rules I live by:
1) Develop a relationship with the landowner or the landowner's descendants (sons & daughters). Not only will this foster a lifetime of good hunting, but I've met some of my closest friends this way. Also a given that you'll soon know more about the land (probably after a 15 minute conversation) than you would after 15 hours of walking.
2) Always ask who & how many other hunters have permission. Always. There is no excuse for not knowing who hunts private property. Come on, it's not only considerate but also safe!!
3) Determine in your own mind how many spots could be hunted on the property. This is dependent, to me, on the following three factors being (a) total huntable land, (b) game population density, and (c) number of hunters.
I'll relate a story to you that proves you need all three factors and the deduction of the last 3 points.
Earned permission to hunt this old farm. Divided into 3 different areas, total land was 150 acres. After scouting the area, I learned that the 60 acres of woods were all swamp, and that 60 other field acres were too close to dwellings and therefore unsafe.
All of a sudden my "huntable" land went from 150 down to 30 acres. Birds were not found on the 20 acre piece of field adjacent to the swampy woods. The birds were only located at the distant corner of a single 10 acre field. I had access to no woods, only the field. My huntable land was now down to a mere 10 acres.
Having a good relationship with the landowner's son, I soon learned the pattern of the turkeys, and this 10 acre piece could be a goldmine. At least 4 gobblers, a flock of hens and various jakes had been spotted prior to season.
The good relationship also spurred them to call me about allowing another hunter access. I had informed them that only 10 acres were really huntable, and the access was limited due to the property configuration. I also informed them that this was my backup property, so I would just appreciate the other hunter's phone number so we could converse and discuss strategy.
That season was the toughest I've had here in CT, and only connected on one bird (hooked up a friend on a bird though) and added my first two maple saplings to the wall <img src=icon_smile_big.gif border=0 align=middle> But me and the "other guy" hooked up for a mid-morning hunt and had 'em gobbling like mad. We found out later that afternoon that a 10 foot wire "wall" was recently constructed on the adjacent property, and we would never have coaxed them in that morning.
Follow the 3 guidelines from above, and you shouldn't have anything to worry about.
However, if you can't contact the other hunter (or you're unaware there ARE other hunters), then first approach the hunter and 1) be certain they have permission to hunt there, and then follow 2) first come first serve.
10point, although you sound as if you feel you "deserve" the right to hunt the property, the "other hunter" you mention in your scenario is the landowner's neighbor!! I'm certain that the neighbor has put in his time with the landowner also, and should be allowed to hunt based on the basis of first come, first serve. To him you are the intruder---maybe he's hunted that property for 20 years!
You never know, maybe he mows the landowner's yard, gives his kids horseback lessons, changes his oil, etcetera...you just don't know how much time "the other guy" has invested either, so first be considerate.
S&R