Everyone is different with different abilities and budgets. I still have Leupold VX3 8.5X25 Varmint Hunter Recital that has sat on top of countless rifles. I purchased the scope back in the late 80's and the price tag was around $900.00. In late 80's this was a top of the line scope. I paid once and cried once, but unlike many have stated, I am not hard on equipment.
Now, Back at that time you would purchase a good Remington 700 BDL (Remington once made Good Guns) bull barrel rifle for about $300. I did not always buy glass because I typically never sold a scope when the rifle under it went away for the next toy. I always looked at the scope as an investment and the rifle as a tool.
My recommendation is to buy the best glass you can afford. If you can afford a $5000 custom build rifle then a $5000-10000 scope should not be out of the question. For the guy that buys the under $1000 rifle there is a lot of good scopes out there today for $1000 to $2000. I try not to snub any of the companies, but I try and stick to USA, German or Japan for origin of manufacturing. I stay away from anything made in China, Philippines or Vietnam.
I am going to take a left turn here, but I will circle back around! The most expensive things in life are not always the best! That being said I purchased a Thompson Center Compass rifle on sale at Cabela's (cheap around $200 all in). I stuck a Nikon 3X9 BDC on it that I found on sale at Midway for less than $100. The outfit intentions was a truck gun that I did not care what happened to it. The rifle is in 6.5 CM (Sorry CM Haters, it was my first purchase into the CM craze). I sighted the gun in with factory Hornady American Hunter 129gr bullets (at the time cheap ammo less than $10/box). The rifle consistently shot 1/2-3/4 moa at 100yds. Done and Done, purchased a case of that ammo and have never reloaded a single bullet for that gun.
As I promised and back on track of the original post. Buy the best equipment that you can afford. But, enjoy all the outdoor sports hunting and fishing you possibly can. Teach your children to hunt and fish. Be respectful and kind to the guy or gal that shows up at the range with equipment that is not up to your standards. Everything in life does not have to be $$$ driven!