Many, many factors to consider here. Deeper isn't necessarily better. Sometimes the most overlooked spots are very close to parking areas and roads. Scouting will help you determine if you have any of these spots. Look for sign (especially beds) to help determine if your property may have one of these overlooked honey holes where a mature buck may bed and frequent during daylight. Remember that a lot of buck sign is left at night also. If you can find a scrape that is being hit in daylight by multiple bucks you've struck gold.
Also, sometimes you are just going to have to accept the fact that you will bump deer. If you know that an interior ridge on the property is hot with sign and deer activity, don't be afraid to bump deer in order to get back to where the action is. Sounds like your area is loaded with deer, so its going to happen. Just try to come up with good entry and exit routes that will allow you NOT to bump deer in the immediate area you are going to hunt, if that makes sense. If you don't have great entry and exit to these ridges, you are going to have a VERY limited amount of hunts before the deer are onto you.
You say you have hills on the property as well. Hills can be tricky because you have your wind and you have rising and falling air thermals which can really mess with setups. As you mentioned, coming in downwind of bedding isn't always the best. In hills, a lot of deer (especially bucks) will actually bed with the wind at their backs, while facing downwind. So even though the deer isn't going to smell you, he is going to pick you off with his eyes as you approach. I never knew this until it was taught to me a few years ago, but its legit!
It's nice that's it's only you and another guy hunting this property. Keep pushing the envelope and scout the heck out of it. If you run cameras, don't be afraid to sink a few deep in those ridges on perennial scrapes or funnels and just let them sit all season without checking them. They will give you valuable info for future years. Best of luck this season!!