I’ve spent a little time undocked this week – although not doing anything that will generate new wealth. I’ve been selling off collected loot and excess assets and supplies, such as 75% of my spare Faction Modules. It is a task that fits in well with my current limited play time.
I’ve made 7 round trips to Jita so far. Some of this necessity relates to volume – I’ve sold off a couple dozen ship hulls, but most of it relates to limiting the value I carry in each run in a T1 Hauler to around 500M or less.
In Dungeons and Dragons Online when I want to sell off loot and spare equipment I go through it to see if anything will sell well on the world wide Auction house, otherwise I buff my Haggle skill and dump everything at the Bar Tender on the Guild Ship.
In EVE almost everything has to be sold to another player. You have to decide if you will sell it on contract or on the market, then where you are going to sell it from, how you are going to move it to market and in what ships and volume / value, if you are going to accept a buy order price or list it yourself, how much you are going to undercut other sellers, how often you are going to update your price, how long you are willing to wait, or even if you want to end up refining the goods into their raw ingredients for easier sale. In amongst all that you have to worry about people ganking your haulers, scams, mistypes and misclicks costing you money.
I guess it sounds horrible, but there are so many ways other people can be involved in the process. You can haul and sell your own goods like I am. You could be the person with buy orders looking to flip goods for a profit, you could be someone scanning ships as they pass you in choke points, you could be the suicide gankers who attack rich ships further down the trade routes, or the pilot who picks up the dropped loot, or you can offer hauling services, or have buy orders across regions to save people the hassle of moving things (at a discount of course). There are lots of decisions, possibilities and risk to weigh up. The very market is a sandpit. Or you can play another game where every Bar Tender buys your goods at a set value.
Evehermit 
Your cake slices are considerably bigger than mine. I recently lost an Iteron V loaded to the gunnels with value in what would have been one of many trips. I suppose one keeps repeating a bad behavior until slapped on the knuckles. Now I’m waiting for my Orca to come due before getting any more goods to market.
Ouch on your loss. I used an Orca for some of the ship hull moves, but I tend to move my small expensive stuff in an Exequror Cruiser. Carries 1Km3+ with Nano’s and a useful tank, and as long as you always manually fly, it doesn’t seem to get too much attention.