Generate a completely random choice? No programming language can truly do that. Generating a pseudo-random choice (for nearly all intents and purposes can be used in the same situations), on the other hand, can definitely be done by all (the common ones at least) programming languages. Last time I checked, flhook is coded in C++ which means that it (in my opinion from being a software dev by profession but not having ever opened a flhook file) *should* be a relatively easy change to implement.
On the other hand, I'm not sure if randomizing it would be the best idea. I lean more towards the idea of a separate starting system that has 1-way jumpholes to the 5 house capitals and corsairs/outcasts along with the current restarts available.
This reminds me that I should crack a few flhook files open and play around a bit with them. If anyone reading this has a good tutorial or 2 on it, a pm'd link would be appreciated!
Make a system w\o exits but with 1 station which is a start station from which new player ships undocks and then make 4 docking rings leading to New Tokyo, New Berlin, New London and Manhattan. When you dock and then undock - you do so in a respectful capital system.
+ people will spread around the houses because you'll have to choose between those 4.
- not sure if transferring between [systems] is possible via docking with a [base].
(Or simply randomize the start point for new characters - when you make one you're being spawned at random location inside the space of any of houses at random base. Then if you don't like you can make a /restart)