Oh, for sure, no issues with it as a general rule of thumb as it is clear and easy to apply, just saying if you're using it to compare actual situations where you roll I think applying the +5 is overly generous to advantage. So if making a comparison like Korbin_Orion has done above you should consider that.
I'm not sure I agree that the middle is where you need the most help, surely the higher targets are where you need the most help? Certainly the middle is where you get the best benefit though, and it is likely it is also where you'll have the most targets. Apologies if I misread that statement.
One other thing that you can consider is targets that are 21 or over, with no bonus and advantage you could never naturally roll that high, whereas with +5 you could still make it with a 16+. Just food for thought is all, I like advantage a lot and comparing it to expertise/proficiency is actually quite interesting, to see what point does advantage outweigh proficiency outweigh expertise.
21 and over only is never accomplishable with skill rolls since Critical Hits is a standard rule for rolling damage. Meaning that a 20 showing on the face of the dice is always going to succeed no matter how high the AC gets or how many - modifiers you got moving it below that number. This is why after a certain point AC is actually pointless because your not getting significant gains even if you do stack it to 67-something over "Oh My God" AC. Just getting it so that reasonably few results on the dice are successes is going to basically achieve the same thing. If you can get it to them needed to roll a 17 or above you've pretty much gone above and beyond in the AC department anyway because when you get above that number there are chances that there are things will critical hit you or simply attack in ways that completely avoid your AC altogether. Or they just aren't going to "play fair" in some other fashion.
Now Skill checks have an interesting issue with them which is more what your pointing to with this question. Because of the nature of being tied to an attribute, being tied to proficiency, Having the possibility of Expertise and Something like Advantage for even more complexity. Unlike With Attack rolls in Combat. Or even DC's on Saving Rolls. Not only is your potential range for what is a useful roll of the dice a lot more varied but It's actually possible to have two different conditions that are basically only encounterable through skill rolls. That is the matter of the roll that can never succeed and the roll that can never fail. Both of these are actual possible situations to encounter. Now we don't run into to many actual rolls where we can't fail because those tend to be easily handwaved because of simplicity of the tasks. But it is actually possible to get on rolls we actually do make. The Rogue is the easiest prime example with this and it usually ends up being seen in Stealth although it can actually appear on any of their skills with which they can become proficient and get expertise in. The reason for this is a combination of modifiers from the attribute, to the higher level proficiency to the bonus at higher levels granted for expertise. By 17th level if these are focused together that on Rogue can easily obtain Stealth scores of +17 or more. Meaning that your guaranteed to roll at least an 18 at the bare minimum. And I can hear people saying that 18 is totally achievable with a roll. It may be a low chance but it is possible. But consider at least one other factor that is part of the base rogue package first. All Rogues get reliable talent which means any ability check from level 11 onward in which they have proficiency added to the roll their minimum roll is not 1. Their minimum possible roll is now 10. That 18 that seemed surmountable has instead become at least a 27 without even actually having to physically roll the dice but can go higher. This means that there are some enemies and potentially even some of your party members that are similar level characters to this one that physically can't make a roll high enough to spot you when your sneaking. And there are potentially ways to get skill bonuses higher than +17 (this number is just very easily achieved). On top of that it's not just rogues that can potentially do this. Bard's also get expertise. Rangers under the right condition don't necessarily call it expertise but get twice their proficiency bonus and so on (they actually call it Canny as part of Deft explorer). There is even a Feat that can be picked up to create this situation. The hardest part about these situations if your the one rolling against them is that Not even Advantage is going to help make a difference in any significant way. They've just hit a point that is out of your league. If you were close there might be a little wiggle room but even getting close is hard because even being close to them likely means that you or the enemy are set up in a similar way but for the opposing ability roll. Which if you are then your mostly back into straight roll off territory as if you were working those middle numbers of the bell curve again. And those that can't compete. They are better off primarily focusing on the center of the bell curve as well. The opposite can actually happen because of negative modifiers and we see a version of this in many plate wearers making dexterity checks But we see it in any extreme mostly during various conditions being involved like paralyzed, petrified, stunned, or blinded and other such effects being on the person so that they can't even pass a moderate check or more likely are made to automatically fail a check.
As a side note. Keep in mind that Expertise is primarily going to be better than Advantage is. But you can have both on an ability quite easily. Expertise is better because it turns even small bonuses that come from proficiency into much bigger bonuses. By the time you reach 5th level in a character it is already providing you a +6 to whatever ability it is attached to before even considering the attribute modifier, which is higher than the general rule of thumb +5 from Advantage. And by the time you get up to 13th level or beyond. It's giving you a +10 or even a +12 which is double or more what Advantage could hope to give you. But you can still get a bonus from Advantage on top of it. It just may be at a point where it's not useful.
At later levels proficiency will be better than advantage, and expertise will be better than proficiency with advantage, I'd say at a guess it is level 9 once proficiency bonus hits +4 that the swing happens. Obviously it is always best to have expertise and advantage, but the idea is comparing advantage vs proficiency, or proficiency with advantage vs expertise. Yes there are other things to consider such as reliable talent, but that does not come into the comparison made here.
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21 and over only is never accomplishable with skill rolls since Critical Hits is a standard rule for rolling damage. Meaning that a 20 showing on the face of the dice is always going to succeed no matter how high the AC gets or how many - modifiers you got moving it below that number. This is why after a certain point AC is actually pointless because your not getting significant gains even if you do stack it to 67-something over "Oh My God" AC. Just getting it so that reasonably few results on the dice are successes is going to basically achieve the same thing. If you can get it to them needed to roll a 17 or above you've pretty much gone above and beyond in the AC department anyway because when you get above that number there are chances that there are things will critical hit you or simply attack in ways that completely avoid your AC altogether. Or they just aren't going to "play fair" in some other fashion.
Now Skill checks have an interesting issue with them which is more what your pointing to with this question. Because of the nature of being tied to an attribute, being tied to proficiency, Having the possibility of Expertise and Something like Advantage for even more complexity. Unlike With Attack rolls in Combat. Or even DC's on Saving Rolls. Not only is your potential range for what is a useful roll of the dice a lot more varied but It's actually possible to have two different conditions that are basically only encounterable through skill rolls. That is the matter of the roll that can never succeed and the roll that can never fail. Both of these are actual possible situations to encounter. Now we don't run into to many actual rolls where we can't fail because those tend to be easily handwaved because of simplicity of the tasks. But it is actually possible to get on rolls we actually do make. The Rogue is the easiest prime example with this and it usually ends up being seen in Stealth although it can actually appear on any of their skills with which they can become proficient and get expertise in. The reason for this is a combination of modifiers from the attribute, to the higher level proficiency to the bonus at higher levels granted for expertise. By 17th level if these are focused together that on Rogue can easily obtain Stealth scores of +17 or more. Meaning that your guaranteed to roll at least an 18 at the bare minimum. And I can hear people saying that 18 is totally achievable with a roll. It may be a low chance but it is possible. But consider at least one other factor that is part of the base rogue package first. All Rogues get reliable talent which means any ability check from level 11 onward in which they have proficiency added to the roll their minimum roll is not 1. Their minimum possible roll is now 10. That 18 that seemed surmountable has instead become at least a 27 without even actually having to physically roll the dice but can go higher. This means that there are some enemies and potentially even some of your party members that are similar level characters to this one that physically can't make a roll high enough to spot you when your sneaking. And there are potentially ways to get skill bonuses higher than +17 (this number is just very easily achieved). On top of that it's not just rogues that can potentially do this. Bard's also get expertise. Rangers under the right condition don't necessarily call it expertise but get twice their proficiency bonus and so on (they actually call it Canny as part of Deft explorer). There is even a Feat that can be picked up to create this situation. The hardest part about these situations if your the one rolling against them is that Not even Advantage is going to help make a difference in any significant way. They've just hit a point that is out of your league. If you were close there might be a little wiggle room but even getting close is hard because even being close to them likely means that you or the enemy are set up in a similar way but for the opposing ability roll. Which if you are then your mostly back into straight roll off territory as if you were working those middle numbers of the bell curve again. And those that can't compete. They are better off primarily focusing on the center of the bell curve as well. The opposite can actually happen because of negative modifiers and we see a version of this in many plate wearers making dexterity checks But we see it in any extreme mostly during various conditions being involved like paralyzed, petrified, stunned, or blinded and other such effects being on the person so that they can't even pass a moderate check or more likely are made to automatically fail a check.
As a side note. Keep in mind that Expertise is primarily going to be better than Advantage is. But you can have both on an ability quite easily. Expertise is better because it turns even small bonuses that come from proficiency into much bigger bonuses. By the time you reach 5th level in a character it is already providing you a +6 to whatever ability it is attached to before even considering the attribute modifier, which is higher than the general rule of thumb +5 from Advantage. And by the time you get up to 13th level or beyond. It's giving you a +10 or even a +12 which is double or more what Advantage could hope to give you. But you can still get a bonus from Advantage on top of it. It just may be at a point where it's not useful.
At later levels proficiency will be better than advantage, and expertise will be better than proficiency with advantage, I'd say at a guess it is level 9 once proficiency bonus hits +4 that the swing happens. Obviously it is always best to have expertise and advantage, but the idea is comparing advantage vs proficiency, or proficiency with advantage vs expertise. Yes there are other things to consider such as reliable talent, but that does not come into the comparison made here.