So I am probably too bored (and hopefully I don't insult your intelligence) but...
If I were starting from scratch, going into new territory, having seen only available imagery and contours, my starting assumptions would be that potential night time food sources are green fields off property to NW (assuming N is up in the pic), just south of property in bottoms, east of property in bottoms, and the four green outlines you put on the picture. No idea where the "in forest" feeding areas are without some knowledge of tree species or understory density so that intel has to be gained "on the ground".
Orange ovals are where I'd look first for terrain based bedding. Cover, etc, plays a big part in whether they are actually there.
Whether the road running north to south along the ridge top/across the center of the property is public is a big factor, but I'll assume it's limited to you and possibly your neighbors.
I usually look at rut travel routes first, because they are often the longest predictable lines of buck travel for me. Bucks are generally going to skirt the downwind side of as many places where they expect to find does as they can. Where they can they will combine that with following a break in the terrain (the military crest everyone talks about, the point of a finger ridge, upper end of a steep ravine, etc). My common prevailing winds are south and west. Dark red freehand lines are a couple of routes I'd predict morning buck travel on a west wind in the rut. Yellow are routes for a south wind but otherwise same scenario. Then I go back and fill in the direct bed-to-feed routes (green).
If scouting on the ground bears out my assumptions, potential ambush points that take advantage of as many potential routes as possible start to become obvious on my scribblish.
On a west or southwest wind, location 1 looks great, provided I can access it unobtrusively.
Locations 2 and 3 should be low impact access, but they assume that the road is basically private. If it's not, they are plenty close to the road for my taste.
4 could be pretty good too, but is really in the middle of places deer have potential to be so most wind directions pose some risk of alerting deer.
With all that said, given that this is 300 acres, you can surely fine tune those buck travel route guesstimates as you zoom in and can (potentially) see variation in cover types better.
And all of the above might only be worth what you paid for it.

Thanks for letting me play.
