What have you done to make money? It is true that bad set of initial guild quests can set you back. Some people just restart. But you don't need get 500 Rep points with the Servants, so don't side with them. You get 100 Rep with the guild you side with. Also the Servant quest tend to be the difficult so do them only if they are easy. Before the second week starts, set all the guild quests to level 2. These give you more money and Rep. You do need to get gear -weapons, tools, armor, and also materials. There is a fairy available for recruiting in one of the forest towns, go find her and set her to fishing . You did set your starting characters to like fish, yes? Or Maverik said he envisioned her as a prostitute, so do that. Dungeon delve, get the first aid skill, buy bandages. Much better than healing spells. You need upgrades to the mansion, there are two upgrades that make building upgrades faster, build at least one of them.
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Yeah i figured about the servants rep during my second run because, well she is the one to give out the quest in the first place. I always make fish a liked food because its easy to get. my main issue is the slave and crafting quests that pop up way too frequently
Edit: I also don't think first aid is that great for me since i spec HEAVILY into magic and each cast heals me for half of my health.
Yeah, I don't invest heavily into magic so first aid is important. Bandage are cheaper that life shards, but aren't found in dungeon loot. One character that I load up with mage classes, one with holy classes, but mostly combat classes. Don't usually have difficulty soloing hard dungeons after a while. One thing I did at first was maximize charm factor on my MC no matter what my other plans were for the character since it increases the money and rep from guild quests. I don't do it so much any more since the factors are now important for many classes and maximized factors give unique bonuses.