It seems like we're all talkign whitetail here so lemme throw in my 2 cents.
I grew up on Long Island, Spent almost 10 years upstate, moved to VA and have hunted VA and MD as well.
My takes: LI can be tough. I was fortunate to live within a mile of 10,000 acres of state land so I knew it well and you could get it done, but iut was much harder at the popoular spots. Some places hacve a ton of deer thoguh like montauk and the hamptons.
Upstate NY: Adirondacks - stupidly hard, rough terrain in alot of places, unpredictable weather, remote, low deer density. This place is hard to hunt. I'm talking wilderness areas not farms. I'm talking High Peaks region. This is by far the hardest hunting I;ve done.
VA - I'm in northern VA and I had a 20yd shot my first day out on public land, and a 4yd shot in the same spot the next weekend which I took successfully. The deer are everywhere, I've snuck up on them in parks and such while carrying my Pug (read 'small wheezing land whalrus with wagging tail"). It's silly sometimes.
MD - I'm embarassed to have so many shooting opportunities in one day. I hunt a suburban private property surrounded by million dollar houses and I see 15-20 deer a day, probably 5 or more in bow range. It's ridiculous, unlimited doe tags, 3 bucks a year.
Anyway, Adirondack big buck, especially late season when the weather is rough, in a wilderness area .... Man if you can get that done, you're next challenge should be flapping your arms to fly.