From DH rules pg.6

Retiring Investigators

A player may voluntarily retire an investigator with two or more total Injury and/or Madness cards. The player simply skips his turn, announces as though his as though his old investigator had been devoured. However, effects that trigger from having been devoured (such as Glaaki's ability to raise th terror level by 2 when an investigator is devoured) do not trigger when an investigator retires.

My question is should it say, "skips his next turn" because to me the way it's worded seems like you could retire your investigator during the Mythos phase ("skip your turn" even though it's the end of the turn so your skipping hardly anything) then have a fresh investigator ready for the next turn without really losing a turn.

I've always played it that you have to skip an entire turn.

I play and promote that you should decide during your Upkeep phase and skip the rest of that turn. However, there is nothing official in here that I recall.

MrsGamura said:

I think the wording is clear. You can't skip your turn in the middle of it, you're already there. If you are playing Monopoly, and move, but then don't buy anything, you haven't skipped your turn, you just did a part of it.

For instance, going insane or getting knocked out can make you loose "the rest of your turn," but that's different than "your turn." The way it's worded, to me, implies what ColtsFan76 said, that it would happen at the beginning of your upkeep.

Retiring Investigators

A player may voluntarily retire an investigator with two or more total Injury and/or Madness cards. The player simply skips his turn, announces as though his as though his old investigator had been devoured. However, effects that trigger from having been devoured (such as Glaaki's ability to raise th terror level by 2 when an investigator is devoured) do not trigger when an investigator retires.

My question is should it say, "skips his next turn" because to me the way it's worded seems like you could retire your investigator during the Mythos phase ("skip your turn" even though it's the end of the turn so your skipping hardly anything) then have a fresh investigator ready for the next turn without really losing a turn.

We play that the new investigator must be ready to go (card filled out and all investigator cards added without bothering anyone else) at the beginning of the Mythos Phase. This is not a rules answer but a convenience answer. Usually an investigator retires (a rare thing) as soon as his turn is done and right after receiving his 2nd I/M card.

It appears that most players read this as "at any time after an investigator has two or more total I/M cards". It might be able to be read as "at the moment an investigator receives two or more total I/M cards, he can choose to retire". This prevents the temptation to pass over investigator items then retire. In other words, if the investigator doesn't retire immediately upon receiving his 2nd I/M card, s/he has to wait until s/he receives her 3rd, etc.

The harsher the better?

Still having trouble with retiring investigator timing, recently played a game where “Aschan” Pete was brought in after another investigator was retired. The AO was Shudde M'ell and River Docks was closed due to World Cracking. So Pete stared off in the street! So how would it work if a monster moves on him?

~Do they ignore on another?

~Monster stop on Pete but they don't fight?

~Monster stops and they fight?

~something else?

...after all it does say skips your next turn...I'm tempted just not to place the investigator on the board during the turn they "Skip"! Would make things easier!

I would play that they fight.

What you are doing is getting your bearings so you don't move, you don't have encounters, etc. But the monster still moves and still engages you.