To give an idea of what I consider to be a reasonable start, I am now up to Nov 3302 in my game, i.e. almost three game years. I started as a Peleng Merchant. This is on 143% difficulty, which is essential Hard but with normal Dominator strength. For most of this time, my money has hovered around 5,000 - 10,000, but I've finally got it up toward 15,000 now. This is still very small. I am now in a position to consider buying a new hull, because 285 is just too small.
I was able to do several 'fed-ex' missions due to my comparatively high jump distance (30 with Farstar micromodule). I have completely avoided attacking any ships, which means no hitman missions, and I've also avoided defending freighters etc. I usually pay pirates if I can't outrun them. One tip with the fed-ex quests: you can ask for easier or harder versions of the same mission. Quite often I found that the destination system was within my jump distance, which meant I could always reach it in less than a month. This meant I could take the harder option for more cash.
The other easy way to make money is doing the real-time battles. These are most commonly available in systems that have just been liberated from the dominators. So it can pay to visit a system that the coalition is attacking, try to shoot a small Dominator ship (like a Shtip) in order to get a reward AND then another reward for the RTS battles. Oh and you should be picking up Dominator equipment and selling them at science stations. But sometimes you will enter a system and see four Equentors (the biggest Dominators). Then it's time to run.
So I finally upgraded all the equipment I had, which means I have some fairly good stuff for this stage of the game, but now I need a new hull. Size 350 or 400 is required for now, and it's important to get one that has all the equipment modules. These are most expensive, of course.
EDIT: if you get stuck on a text quest, here are the solutions. This is from the now defunct Elemental Games forum. There are a few new text quests in Reboot that aren't covered here. I recommend trying all the text quests yourself, but a few of them are fiendishly difficult and may need a spoiler:
http://www.elementalgames.com/forum/...e=42&page=auto