Not necessarily! I killed a 5 year old 10, 3 years ago and my buck this year (6 yr old) off a 40 acre piece (mostly CRP). Pressure on 3 sides. Plant food and don't hunt it until it's right, and you will have big deer. The one nice thing about Iowa is that you don't have to have a big chunk to kill big deer. Sure they wander, all of the neighbors had seen and were hunting the buck I killed this year. With the last and best available food source, we had the does, so he always came home.
Man Dedgeez, we're of incredibly similar like mind, are you my long lost twin my folks lost at the hospital all those year's back?!?!
I'd say of all the bucks we've killed that are mature, 75% or more have came off of smaller farms or farms that are not "premium managed" places with plenty of folks hunting them. Was it harder to get and find them- SURE THING! But- we found em each year- NEVER is easy on any tract but they can be found on small tracts in many areas. Loneranger has a tougher neighborhood to hunt & get mature deer BUT obviously he proved you can get whoppers on small tracts, I sure was impressed with the 2011 photo recently from him!!!
Judging a deer that is passing through- happened all the time hunting little tracts.... That's usually what we hunted- deer we never saw before. Heck, I had no trail cams 6 years ago and then for 2 years after that I only had ONE. Most deer were totally new to me. There's obvious knowledge acquired from being out there and doing your homework, education and research on how to effectively age deer. When I was 14 years old- NO WAY, I sucked. After 19 more years, yes, I know what I'm looking at. Exact science? No. But- can someone gauge: snout, body size (varies- sure), color of snout, etc, sagging skin, chest size, antler size/mass- etc, swaying back, dominance in presence of other deer, etc, etc, etc?!?? Of course. Lot of material and education to be had on this topic. I'll NEVER have this perfect, NEVER. Nor will most I know judging a new deer they see BUT I think most folks who take the time can be right most the time and if wrong, MOST of the time be off by only a year. Is it the most critical thing to hunting & enjoyment- no BUT it's sure a useful tool of knowledge to immensely help in management, biology and helping make decisions on what to shoot for some.