Well I am pretty aware my turtling player's issues. They are many, turtling is only one of them. He prefers AD&D, I prefer D&D3.x. He complains a lot. For one he has issues about how 3.x nerfed magic. Ok, but then he goes on complaing about some powerful spells. And yet again when he runs/plays AD&D he uses the most irritating spells there is (hold person, ironguard, stoneskin, flesh to stone, contiguence-spells, etc. His real issue of course is he knows his houseruled 2nd edition AD&D well, but can't make even normally effective characted in D&D 3.x. He tries to go for too complicated things, same problem why he stopped whiningly playing starcraft. He was always planning tactics that would only work if enemy left him alone for long time.
He also wants nothing bad ever happens to his character and yet wants game to be interesting, but doesn't want it to force his character to do anything.
I have asked him many times what kinda of game he wants to play (I have no problem to change system) and he starts to whine about some ages old games (most of which I was not involved any way) and generally intrupts game often to talk some pointless stuff (and irritating jokes made by other people times past). Sometimes he actually enjoys the game, but despite feels need to whine about things "that might happen":
He was kinda like that, but not as badly as after playing 7 years of wow. That killed that bigger group into 4-5 people. I don't think our current playstyles are good match. We play togeter for old times sake, and because we are friends, and because they don't have any other people to play with. Honestly because I and my 2 other friends are only ones that still want to play rpg:s with them. Whiny behavior without saying what is wrong or what he would rather play. I think it just might be he doesnt' like table top games anymore. As they are too unpredictable.
Honestly with him, only thing to do is either stop playing/play when it works. His dm:ing is best for 2-3 sessions then he gets attached into our character, stops running modules and game starts to suck. So there is more peer pressure to make him continue running modules. He never cheats as player, but he tweaks (cheats) combat all the time when dm:ing, we are killing mobs too well, oh, hp and ac goes up. We are in danger, suddley mobs start to die very easily. This doesn't happen (except to save us) when he is running modules. Also his own adventures try to steal us away forcibly where action is, often by some random time travel. I like time travel in time travel games, but he only does this to keep us in some dumb village for year "because we can't do anything or we disturb the timeline". If we still try to, some universal correction thingie puts us back to track.. to do nothing. Oh we can get some professions in village and do some boring stuff, but as he is not also very good at playing npc:s or likes character-action, and doesnt' like "finding lovers or even friends" stuff. It really suck. We have quit 3 games that got us into stagnant situation. And he doesn't get what is wrong and argues back to me when I call it boring. He sometimes quits games too himself as he can't come up with more things.
Maybe next time I should run some AD&D game with freedom to do anything and some availabe dungeons to investigate. Without any plot to confuse him. Yeh, it might work. His character motivation could well be need lots of money to happily retire. It just might be, I have started to think after reading this thread, that his problem might be he wants back to some pure and innocent days of dungeon crawling with gaming system of those days. Honestly AD&D has different feel than 3.x.
Problem with this is I don't have time/energy to even read let alone create my own dungeon adventures. But maybe I would pre-read like 3 modules and let him choose one of those and if not I would whip out my random encounter tables.
Though he really likes 2nd edition AD&D (which I am mostly ok with) and Forgotten Realms (which I refuse to run). 2nd edition Forgotten Realms brought in my mind some annoying complexity that kinda ruined the game for me. I ended up playing lot of other games until I finallly got back for 3rd edition. Which I like, because I enjoy the character building and how system runs.
So we can't agree on which complexities are cool, so maybe simple gaming brings fun back. Yeh, all hope is not lost. I think I try this, honestly I have trying to force too much of my game system preferancs on him.