Since it is generally understood that you
want some (at least) minor spoilers when you ask a question about the game, let me reply more usefully to you.
Your first question is pretty much impossible to answer without a walkthrough of the game - it is your primary goal, after all. If you
really want a walkthrough,
Slayer's Guide to Cythera can do a better job than me of giving it to you. It also has other resources.
As to your second question, you can be joined by (in addition to Hector), Aethon, Meleager, and Timon. Aethon can be found in Cademia, Meleager on the bridge near Cademia, and Timon in the ruins to the northeast of Pnyx. Timon will join you only after you have registered the game.
As to making money - ruffians are generally fairly poor, but if you find a good concentration of them (like their encampments, which can be found in various places inland on Cythera) you can make out pretty well. You can also make money trading. Hebe in Odemia will buy flax, and there is a flax farm on Cythera that sells it.
Also, the tip "Just keep going after the tasks on your to-do list" is very good advice in general.
Enjoy the game!