hurvl: It's funny that you mention having problems with a jack of all trades character in the first Dungeon Siege, since I remember that in the Dungeon Siege 2 demo I played when the game was new (which contains the beginning of the game) you specifically get an advice from an orc-ish looking NPC to specialize yourself, because otherwise you'd become a "worthless jack of all trades".
In the beginning of DS (base game) there is a temptation to train your main character with two or three "trades" especially because you'll be playing single for almost the whole first chapter IIRC. You meet your first potential companion at the end of chapter 1, and quite soon after that you actually have several more potential companions.
So in the very beginning you probably just start hitting enemies with your knife as a melee fighter, but soon you think hey maybe you should use the bow instead at least for some enemies so that you don't have to go near them, and hey of course you want to heal yourself with spells as well, so Nature Magic as well?
Also, some instructions or FAQ mentioned that you should train your magic users also as melee fighters so that their strength gets better and hence they can also use more advanced armor.
But all in all, the problem is that enemies don't respawn, so you have only a certain amount of XP to be gathered throughout the game (I think almost all of it comes from combat, I'm not even sure how solving quests help your character, other than getting some money and special items maybe). This is made even worse if you intend to have many companions (up to 8 characters in your party) because they have to divide all the available combat experience points between themselves, depending mostly on how much they deal damage to enemies in fights, AND someone here also pointed out that if you play the game in harder difficulty level, you get less XP, hence you level up less often. AND, I think I read in some FAQ also that the game discourages you from trying to improve several "trades", by making sure the weaker skills that are lagging behind take also longer to improve.
So I think being "jack of all trades" makes sense only if you are going to play solo without companions (then you also level up more often, I guess). I chose to have the max 8 characters in my party, playing in the hardest difficulty, and even though I tried to find all the enemies within the game to kill them and gain maximum experience, by the end of the game the highest and best armor, weapons and spells were still far beyond the levels at which my characters are.
So, it does seem that if you want to get to use the best equipment and spells in the game, you need to severely limit the number of companions, and/or play in the easier difficulty levels. Sad but true. And if you started making your characters jack of all trades, you'd be even worse.
However, while playing the expansion pack, I did suddenly realize something: regardless of specializing, you should still give all your characters (from melee fighters to archers to all magicians, doesn't matter) the Healing Hands spell (which is part of Nature Magic). The reason is that that healing spell has no magic level requirements so everyone can use it from the start... so why not let everyone use it then between fights, to let everyone heal each other? Works great, and it doesn't really matter even if their Nature Magic skill doesn't improve much from that one spell.
In the base game I had two dedicated healers (concentrating on Nature Magic, also using attack spells), but now I realized that isn't really needed. One specialized Nature Magician is enough (even if that), and simply give everyone that Healing Hands spell. Then everyone is also a low level healer, even without health potions.
hurvl: I've sometimes thought that I should play Dungeon Siege 1 and 2 (the third doesn't seem too good), but I'm annoyed that Legends of Aranna isn't available digitally and I've got lots of other games to play, so I never played past the demos.
Yeah I first started playing my Steam version of DS1, but when I realized it doesn't have the expansion (Legends of Aranna), I took out my retail version of DS1 which has it. Fortunately I got it to work fine on Windows 7 at least.
Legends of Aranna basically feels more of the same, a separate campaign from the base game where you start from the beginning again (I think you are adult child of the original character you played in the base game, or something like that, if I understood right). There are some new things like apparently some new spells and the teleport platforms which make it quicker to get between certain places (when e.g. backtracking), but mostly the same as the base game.
I am unsure if the Steam version of Dungeon Siege 2 is also missing the expansion (Broken World), I need to check that... I think I have the retail version as well.
