D&D 5E - Thoughts on a skills PC.

Whatever you decide on (and best of luck with finding your best choice)... the thing to remember though is that none of those ideas are going to solve or remove the biggest issue when it comes to skills... the d20.

Having proficiency in lots of skill is great... but even then your best bonuses at Level 1 will be like a +8 (+4 with an 18 ability score, and +4 for Expertise's doubled proficiency.) But when you add that to a d20 roll... that 20-point swing is going still give you lots of times when your check is barely a 15, sometimes even less than 10. And quite often you will find times when your tricked out skill monkey character still gets beaten by other members of your party who have stacked up on combat instead because they just happen to roll a 19 and you rolled a 3. That kind of thing happens all the time, especially when there are four or five other players all rolling the same check you are. One of them has a good chance of beating you a lot of the time and that can take some of the fun out of being the supposed skillful one if you keep noticing you still get beaten on checks.

I'm not saying you shouldn't make this kind of character... if you think it will be fun you absolutely should! All I'm cautioning is that because of the swing of the d20... failures are still going to happen and quite possibly more often than you might otherwise think with a "skill-focused" character in the party. But at the very least, having that character will reduce the number of failures your party tends to suffer from (even if it can't eliminate it completely.) Hopefully those additional successes will be enough to make it feel like it was worthwhile!

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