How about trying the opposite approac with the rules? Rather than require him to list what actions he's doing in DnD terms (damage to the window followed by climb check etc), get him to describe his action.
Him: "I break the window and follow the BBEG"
You: "I can't visualize this. Are you stopping to break the window with your sword, or diving through the glass, ignoring the shards in your haste, or something else?"
Him: "Well I guess I'll stop and break it."
You: "Okay, make and attack (give the AC) and do at least (some Damage). You broke it? great? That's your turn. While he's doing that what are the rest of you doing?"
Nother Dude: "Busting through the glass of the other window with my move action, I make the burst DC easily, and since I have enough to get next to him with one move action I'll use my standard action to attack. Oh, a hit!"
You: "Great roll damage. BTW, you took 6 points from the shards of glass."
Him: "That's what I wanted to do!"
You: "Hey, I asked what you were doing, you said you were stopping! Who's next?"
There are always tactically advantageous options, but it drives me nuts when players spend 10 minutes picking the absolute best, or whine when they "didn't get enough info to make the right choice".
Ask me questions if my description is unclear, but don't piss n moan b/c I didn't specify exactly how much damage you'd take from the glass.
When he goes on an incredibly detailed description of knot tying, just say (gently), "look, this is cool. I could never remember how to tie a timber-hitch, but you're character is going to be tying this knot with his "Use Rope" skill. Your personal knowledge is not going to affect the DC for your PC."
Him: Piss moan
You: Look, if you want him to be good at tying knots, put some skill points in Use Rope.
Gosh, this has gotten long.
Last thought. Make EVERYBODY esponsible for levelling up their characters. That way he can't pass the buck if whoever chose skill points didn't do it according to his "vision". If you take this route though, you will need to review characters and make sure you're open to answering questions.
I'm a softie, so if he were REALLY bummed about accidentally putting all of his skills into Jump (or chose the wrong feat), and felt useless, I'd let him redo it the NEXT session...
...with an XP penalty.