D&D 5th Edition Stealth Issues

 Well, I did promise that I'd talk about D&D 5^th edition's stealth system. So, let's get right to it (naturally this will be system specific). Also, I'll be using some of the stuff I mentioned here.

Group Stealth Checks

Group stealth checks aren't really mentioned in the rules as they are presented. At the same time, some adventures sometimes use group stealth checks. On one hand, you can argue that a group stealth check makes sense since the stealthier characters can plot out paths that will attract the least attention. On the other, they can make sneaking easier in some circumstances (two stealthy characters together). The easy solutions is to set a minimum number of people to use a group check as well as a maximum number of people (if there are 10000 of you, they will see you) or just leave it as is.

What Does That Say?

I've been reading and rereading the stealth rules for this edition of D&D and ... I've basically given up running them as written and just cobble together my own system. The other activities section (page 65 of the basic rules) for traveling says that when a player is doing an alternate activity, they don't contribute their perception checks to the group. Does this someone performing an alternate activity get instantly surprised or is there some unmentioned way for characters who don't notice the stealthy enemy to be warned by their allies? I like the idea of being able to warn the rest of the party (fail the stealth check by 5 or more for example?).

Expertise

The expertise rogue feature on perception and stealth checks gives a massive advantage to those checks (when combined with other features, it gives them a very impressive minimum value for stealth checks). If the party ever faces similar characters (especially if the Dungeon Master tries to build a rogue using the player rules for the party to face), there is a large chance they will be surprised. I've seen almost the entire party take the alertness feat just to avoid it in games that involves a lot of stealth.

Solution

A solution for this isn't really that easy. It seems the intention in this edition is for the Dungeon Master to determine when surprise is appropriate as well as when it makes sense for characters to sneak past. There is nothing wrong with that but as written it can make things rather strange. To help some people out, here are some options:

1. Failing a stealth check by 5 or more allows that character to warn the rest of their group (solves the case when players do other tasks too)
2. Group checks are allowed for a group to sneak. Their check is equal to the the middle value. In the case of an even number of characters, go up (in a group of 4, the second highest value is the groups result in cases where the value is needed for later)

Areas like rogue's expertise are more challenging and need to be decided with the rogue player themselves. You could also decide that it is fine as it is, but I still find it kind of weird in it's current form at high level play.