The definition of overpaying in pro sports is not cut and dried, especially in football with its complex depth chart. There are no set numbers, but of course there is some basic math. You have a cap (or at least a budget) and you subtract a few expenses and some planned wiggle room and you divide the rest by the roster size. That gets you a guide to average pay. This is a very loose guide of course because each position is very different and players have different roles and some are rookies or young players and some are seasoned veterans. But if you cap say is 5.8 million and you have 10 practice roster spots at 30k per year then that takes you down to 5.5M. Then you want some wiggle, so you figure that you need 300k for that so that gives 5.2M. 5.2 / 46 (roster size) = 113k each. Now your star players are going to make much more than that so your average player will make somewhere less than that. This means that most players will be making between league minimum and 100k. So if you are paying someone 95k that is a very average amount of money. If this player that you are paying 95k is starting, playing well and giving you a veteran or veteran-like presence, then you are getting a bargain. If he can barely get off the special teams he is overpaid.
Most people agree that the number one skill that a GM has to have is evaluating talent - looking at a guy play and assessing how good he is and what he can do for you or someone else, and I won't disagree, but grossly overlooked is the the number two skill needed - in fact I would not call it 'two' but 'one-a' - is appraising a players value, or knowing how much to pay a guy, knowing how much is too much, and spotting undervalued bargains.
To do this you have to compare a player to everyone else that's in the talent pool that plays his position and/or performs his role. If the player is head and shoulders the best player at his position/role then pay him top dollar. It's worth it. You will have an advantage over all of your opponents that they cannot make up. If the player is the best at his position but there are several others say 90-95% as good, you can get someone 90% as good for 60-70% of the price. It's an opportunity to get value - a bargain. Otherwise, sure you have the best player but you are paying extra for very little advantage.
If the position is deep (saturated with talent) don't spend big money. Save that for positions that are hard to fill. It's really simple supply and demand but there is a zen to it.
The easiest position to fill is RB. You have one starter and there are tons of guys out there who can carry the ball and make things happen simply with athleticism and instinct, especially if your offensive line is decent. Lots of ordinary guys have rushed for 1000 yards for one or two years and disappeared. Supply of RB talent is high and demand is low (you need less of them) so the price should be low.
Receiver is another where there is lots of talent out there but it is still much harder to fill than RB because you need so many of them. Supply is high but demand is also pretty high so the price is more moderate.
Defensive tackle is very tough to fill. You need a big athletic guy who can take double teams and cover run gaps. A guy like Doug Brown or Tyrone Williams who can dominate in the middle is rare. At any given time there may only be two or even one of those in the league, so if you find one, pay that guy. You will have a serious leg up on everyone else. Supply (of really good ones) is low, price (of really good ones) is high.
Decent and even good linebackers are everywhere. If you're not careful you will trip over one. In following the CFL for over 40 years I have never seen an LB who is miles better than any other LB. Why pay Adam Bighill 200k or more when you could pay Jameer Thurman 120-150 (or even Keyshawn Bierria 100)? Bighill is fantastic but he is nowhere near twice as good as those other guys that I named. I'd rather take that extra 50k (or more) and put it towards Ja'Gared Davis or Stanley Bryant, especially considering that an LB cannot save an otherwise weak defense but a DT just might once in a while. A strong d-line is the best way to make LBs look good. Supply of LBs is high, demand is moderate, price is low-ish.
O-line can be difficult to fill, but not as hard as the secondary. DBs are the hardest to find (other than maybe star QB). They require the most experience to develop their skill set and you need a minimum of five! Any player in the secondary with a weakness in his game will be the first player exploited by the opponent's gameplan, especially when matched up against a veteran receiver. Supply (of good ones) is low, demand is high. The price (for good ones) is high.
Paying Justin Medlock big coin is worth it. Not only is he a top 3 or 4 FG kicker, he has the longest leg of all the top kickers AND he's the only one who also punts. What is better, paying Medlock 200k (and freeing up a roster spot for an extra receiver or DB) or paying Lauther and Ryan a combined 300k?
Some tips:
Don't pay players for what they've done, pay them for what they can do for you now (or the term of the contract offered). This is one of the biggest mistakes (one of Taman's common mistakes).
Don't nickel and dime good players. Do the lowball haggle thing sure, negotiate, but be prepared to pay a fair price in the end. If you want a good player, you will have to pay for one.
If you get enough bargains on your roster, you can afford to use your wiggle room to overpay a little at a key position (such as keep your star QB off the market).