WM has been through major engine overhauls since it's conception. This has delayed any major progress on enhancing any existing gameplay, while this is not a bad thing I think the most important thing WM needs is to become more personal. You don't care about your gangs because they're just numbers going out to do various tasks for you. Whatever your reason for caring about your girls (She's your favorite, she's your best) whatever that may be just doesn't do the same for gangs. Once you max out a gang you can always replace their numbers so there's no real sense of "loss" and since you never interact with the various members of the gangs they don't mean anything to you.
This is not to say girls don't have the same lifeless feeling as gangs do. They most certainly do. Adding a "face" to your gangs would be a start, but it wouldn't do much in the end. And while I don't disagree it would be cool to have your girls be gang leaders, it just makes Crossgate seem like a town full of women. Which I'm pretty sure it is not.
Now I've been pushing for more interaction within the game since it started, so I may be more biased on my thoughts than some of the others, but I have no doubt once we can add NPCs you can interact with, negotiate with, give a face for the governor and various other NPCs as well as gangs. WM will be 100x bigger than it is now. It only feels empty because you simply don't care about anything or anyone. They're all replaceable. Yes, you're a slave owner so you shouldn't have feelings for anyone who isn't paying you right?
But will you be able to turn a woman down half naked covered in bruises, cuts and blood being chased by some thugs?
Do you ignore her or help her?
You beat up the thugs, rescue the damsel allow her to heal and rest in your home. Then the next day you find your vault was broken into and you're 10k short. The girl? Nowhere to be found.
I'm sure a solid scripting system will change all this, imagine what the community could do? Can you even think of how big this game would be? Hell, with a solid scripting system you can lay the foundation to your own story, own events what have you. It'll be pretty much an open book for creativity. You could essentially make your own game from it.
I personally think all WM needs at the moment is more of a narrative, allowing us to use images for NPCs and interacting with them.
As it stands WM is a fairly solid game, there's some balancing problems, there isn't much to strive for but that could be addressed at another time, it just feels very very empty. Modders are flooding it with girls to try and make it seem less barren but the fact of the matter is, there's nothing to keep the player playing. You have to make your own imaginary goals.
After getting SLIGHTLY off topic I would like to say giving the gangs leaders would be a viable option, it'd be silly to give the whole gang a face and interact with them, but more so a leader, captain, commander whatever you want to call them. Would be the person in charge, this person would offer various boosts to the current gangs stats and abilities. (+10 to strength, bonus to kidnapping ect.) They'd only need a single image to portray that they're the leader and you could even add a bar area where you can find these people. Instead of having random ones though, i'd make them all fairly unique and very limited I'd say only allow 5 you can recruit to exist in any given game. Perhaps that's too many? I'm not sure. I suppose that it could also be a role for your sons. Who knows?