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Well, Mediocre success. I managed to fully impliment Pirate military convoys, however, my original plan called for the military convoys to be divided into four tiers, starting off with the rookie stuff and eventually ending with very high-quality gear (well, for pirates), with the level of escort determined by the quality of the goods inside the transports.
However, RandomContacts really, really, -really- dislikes tiered systems, and unless I modify large sections of randomcontacts.script (which I am not comfortable enough with Lua to do). On top of this, I had difficulty getting any of my scripts to work properly. They would properly add modules to a ship's inventory, but for some odd reason they would not add ships despite having the correct function.
I eventually gave up, and decided to modify the already-existing FillTraderSimple function to my needs. It works, quite well actually, but it means that the tiered system I originally planned for is gone (Although it works with randomcontacts now), thus all Pirate convoys are rather heavily guarded with Third and Fourth generation ships.
The only thing that is left is to clean up the mess I made a little, and impliment convoy fleets for all the major factions, and than modify all the location scripts so that they spawn.
So far, I only plan on introducing USS, Triada, Inoco, Patrol, Pirate, Old Empire, and New Empire convoy fleets (the remaining factions are too small to bother with). Convoys will be heavily defended, Pirate and Patrol convoys will have mainly third and fourth generation ships (mainly because neither faction has any fifth generation ships), while the rest will have fourth and fifth generation ships guarding them (corporates would be more fourth-generation heavy, while both Old and New Empires would be heavier on fifth generation). Loot inside the transports is randomized, and can be anywhere from First generation to fifth generation, weapons are randomized the same way.
Convoys will be mainly located in systems where the faction in question has a strong presence, mainly to prevent the situation of free loot coming about because an MSF fleet stumbled upon a New Empire convoy.
Ultimately, the reason why I implimented them is that I wanted to give the player more ways to acquire fighter hulls other than either buying them, or attacking a faction's warehouse for them. If you do not like a faction, you are free to whack their convoys for free ships and loot, and even law-abiding neutral citizens can join in the fun by whacking pirate convoys (Although Pirates and Imperial Patrols generally have lesser loot, you wont ever find any fifth generation ships)...
I am considering adding an SOS system for Military convoys, but that might be thinking too far ahead.