The Demoman is a truly formidable weapon on offense. Although it may not seem that a Demoman would be able to take out a Soldier with full health and 200 armour, a truly skilled Demoman should have no problem doing so. The trick with the Demoman is to know when to use pipes, and when to use regular grenades on offense.
Pipebombs
The bottom line with pipebombs, well, with any grenade, is that you have to remember where you put them. I can't tell you how many times I've seen a Demoman loose a battle because they forgot where they put a grenade or a pipebomb, and they just walk over it when it goes off. I use pipebombs 99% of the time when I play Demoman. I think they are much more reliable than regular grenades. At long range they are a great weapon because you can time when they explode. Check out the defense section for information on how to bind keys so you can detonate your pipebombs.
Weaving
Weaving is a strategy that I use both inside and outside. However, this will only really work if the area where you are fighting is large, such as the space outside the base in 2fort5.
Ok, let me create the scenario for you: Lets say that you are fighting a Soldier. Instead of just firing pipebombs at the Soldier and pulling the trigger when it reaches him (which does work by the way), "weaving" is basically trying to get the Soldier to forget about where the pipebombs are. When you weave, you fire the pipebombs towards the Soldiers feet. If they reach him and you still have time to pull the tirgger, then go right ahead. However, if the Soldier is too close, you lead him in a huge circle, and when you get back to the first grouping of pipbombs, you peel off, and when he walks over 'em, pull the trigger. It's hard for me to describe it, but check out the pictures:
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Use the Walls
This strategy can, obviously, only be used when there's a wall convieniently available. To use this technique, you have to know your geometry (yeah that's right...math even figures into TF!) But it's ok if you don't know geometry that well...hell I got a D+ my Freshman year! Anyway, let me setup a situation for you.
Ok, you're inside the enemy base. You've got your pipebombs ready (I use 'em 99% of the time), and you start heading down the enemy ramps to their basement, when another Demoman starts chasing you! He's too damn close for you to fire a pipebomb right at you, and he's weaving around, so a normal gren might not even hit him. So what do you do? Fire your pipebomb right off the wall nearby. So instead of the pipebomb being far behind the enemy when you detonate it, it's sitting right in his lap when it explodes...ouch!!
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This strategy is not limited to only the ramp room of course. It can be used in many indoor places, an optimal time would be if there is an enemy around the corner, just fire a pipebomb into the far wall, and let it ricochet right to where he is, then pull the trigger.
Hide your pipes
One of the best things about a pipebomb is that you can put them somewhere...and just leave it there. Ok, lets say you just walked into a room, and a big, bad Soldier is standing there with 300000 armour. He, of course, starts to fire and chase you. A great thing that you can do is to retreat to a place where you can conceal your bombs in a place where he won't see 'em 'till it's too late.
Take these pictures as another example of a Soldier coming around the corner:
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This strategy will be heavily emphasized on defense as well.
Normal Grenades
I really don't use normal grenades that much. The only time when I use them is when I'm in close combat in a tunnel or something. I trust pipebombs much more than I do normal grenades. The basic strategy with normal grens is aim, and shoot...nothing more to be said. However, the idea of using the walls as with pipebombs can also be applied very effectively to normal grenades. Still, I rely much more upon the pipebombs.