The best way I've come up with for battling the boredom is to do circuits rather than routes. Take item a to destination b. From there take item b to destination c. Continue until you make a full circle. I try to do at least five seperate stops. With a little work you can set up a circuit that never leaves the heavily populated systems while making enough profit to be worthwhile.
The problem with monetary rewards is that we are already being rewarded with credits for trading. More credits just makes it so you do fewer runs, not more. We want people to want to rp, not take advantage of rewards and get done even faster.
Going to take a page out of the book of MMO's. In an instance, flashpoint, what have you, four to five people have to work together to get a task completed. Granted, we're not going to have healers, tanks, or DPS in Freelancer. I get that. But there needs to be a similar goal in mind with convoys.
Maybe have profits be a certain percentage higher while others are trading with you. If someone in your group sells a certain item at a base, another person in your group, who is also trading (have the game do a check to see what they're flying first so it can't be abused) receive a certain bonus percentage of the profits for themselves. This will also help to pay escorts flying WITH the traders (or smugglers, what have you).
Pirates really need to get out more and hit those tradelanes hard. Get the traders all riled up, FORCE them to pay for escorts. That will spark Roleplay, which is always fun. Factions who run escort services should start springing up, taking a certain percentage of the profits for themselves from the traders.
Just some thoughts I was considering when I read the initial post.
~Leo
You fear oblivion. Yet you forget. The universe remembers every atom of your being. Even dust hums your name in the dark.