I'm in a league where I'm giving shots on every match I'm playing, so I'm already behind on strokes starting out.
I make my opponent putt everything out until I feel that I'm far enough out in front that I don't need to be a "Jerk"
I'll give 2 footers and in, past that, you have to make it.

Yeah, I played a buddy of mine on a course where one of the Par 3's was like the #7 handicap hole. It was one of my stroke holes.

He made a decent length putt for par and I had about a foot left for bogey-net-par. I looked at him and he said, "You can have the stroke or you can have the gimme, you can't have 'em both". I thought that was very well stated!
 
Never concede birdies/eagles unless literally a tap in. But the rest depends on how the player has been putting that day. Putting well and the circle may expand. Putting poorly and you may have to putt out a few I may normally give.
 
It changes round to round for me depending on how my opponent is putting. But the only way I'm conceding a 5 footer is if he can 2 putt to win the hole.

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I wouldn't concede anything outside of 2 feet that matters. If it's a putt to win a hole or the match, it might get even tighter. Why would I let my opponent off the hook in a tough situation? It's a different story if I'm clearly out of the hole, or if I have a short putt to win the hole.
 
In our league play/money games you have to putt all eagle/birdies/par putts and all putts to tie or win the hole. Other than that its pretty much anything with the putter grip is in the friend's zone and good. If it's for triple or higher, anything within 10 feet is good. Why make a bad hole worse.
 
Usually that inside the leather range.
 
with my buddies playing for skins, if it is a putt I am confident they are going to make I will give it to them. If not, they have to putt it. I also never give birdies, but that is because personally I want to see it go in so I figure others do as well.

If I am in match play? Really depends. I am usually much more generous early and stingier as the round goes on. It usually has very little to do with what my opponent has given me, but I have been known to not give putts when someone has not given them to me.

But I never let it bother me, if it is a true gimme I could care less if I have to putt it or not since I am going to make it regardless.
 
We always play "in the leather" is good. Sure that distance varies from player to player, but it takes any guesswork out of it, and precludes anyone from taking a putt they shouldn't (I've even done this in match play as long as my opponent agrees). One very effective wrinkle we implemented once: if a player measures for "inside the leather" and the ball is outside of that range, the player who measured owed $20 to all of the others in the group. My brother suggested it, and wound up getting burned on the very first hole. The result of that little rule was that we mostly putted anything that wasn't an obvious gimme.
 
We play inside the leather as many others do. Takes away "gamesmanship" which we don't like, and it speeds up play.
 
One thing I think about early is maybe giving them one on hole 1 from a bit further than normal just so they don't get to see one drop. Even making a 3 footer can build confidence. I would never give more than 4' but I might give a 3-1/2' to tie if it spared them building some putting confidence.
 
Anything inside 2'. No one misses 2 footers. Ironically I can one hand a 5 footer into the hole if I don't care about it. But stand over it? It's a knee knocker.
 
We have a pool of about 10 golfers. When we have a foursome we play a version of Vegas where partners on each hole are determined by each player's tee shot (the two on the left versus the two on the right.) Every player's putter is marked by a piece of masking tape around the shaft and if your putt is within the tape it is good. The length of the mark is about 19" and is the same for everyone. We do it this way so we don't have to worry about the distance from bottom of the grip is different for everyone.
 
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