This would be difficult to code, for starters. Also, at certain places like a Sweatshop or Prison, you can recruit people into your party, up until it has 6 members. If you split into multiple parties, and they all Liberate Oppressed... well you could split an original party of 6 people into 6 parties of one person each, and then each of those 6 parties would be able to recruit 5 oppressed Liberals (such as illegal immigrants working at a sweatshop or prisoners in jail). This would give you the ability to get 30 people to join the LCS, all in a single raid!
Another consideration... while one squad is going around and doing things, what would the other one be doing? Just standing in one place, waiting, right? Well you've noticed, if you stand in one place waiting long enough, eventually other people show up, usually including some Conservatives, and then you'd better have disguise or stealth to avoid getting spotted and alarming them. If the Conservatives ARE alarmed, then how would you manage having multiple separate squads fighting Conservatives at the same time?
If you split up your group, then each of your members could easily get outnumbered by Conservatives. Plus how could the group coordinate their activities with each other? By walkie-talkies or something? That kinda thing makes it more likely for them to get caught.
Also, letting people escape at different times is also problematic. If you came there by car, everyone came in the same car, so if people escape, only one group escaping can use the car, everyone else would have to go on foot. And there might be a chase sequence for some of your Liberals, while other Liberals are still in the building.
What are the real benefits of splitting up, anyway? The things you cited (AM Radio Station and Cable News Network) work perfectly fine having the entire squad explore the site together. Those places aren't that big.
Anyway a Squad is like a team. They do things together. They go places together. If one of them commits a crime, they all get in trouble. If one of them picks a lock, the others can observe this lockpicking and learn from it. It's all about teamwork, for people in the same squad. If you want to go solo you can have a squad of just 1 person.
So yeah I don't think this feature is likely to happen, it would require lots of code overhaul, and we'd need to deal with cases such as what happens with the squads that are waiting in one place, how do we deal with people who leave the place before others, how do we deal with people releasing oppressed such as sweatshop workers or prisoners, how do we deal with multiple fights with Conservatives happening simultaneously, how do we deal with reuniting 2 groups if the total number of members in both groups is more than 6, etc. If we wanted to seriously implement this, we'd need to have answers about how to deal with every single one of those situations, or else the game would have errors if situations occurred which the game would not be coded to deal with. Plus this would involve creating lots more variables and functions and modifying a lot of existing code.
And for what benefit? Very little if any, as far as I can see. Having the entire Squad together works quite well, since they can learn skills by observing each other, they can all take the same transportation (such as a car) together, they don't get outnumbered in fights due to other Squad members being somewhere else, and they don't have to worry about other people who got separated. I don't really see how splitting up a Squad would actually help you out in the game. In the cases of AM Radio Station and Cable News Network, a single squad is quite easily able to deal with any situations that arise at such places, if they all have good skill levels: you can get all the loot, pick all the locks, take over the studio and do a broadcast, all that stuff. The only real challenges at those places are dealing with Radio Personalities and Cable News Anchors, whose special attacks in fights can turn your folks Conservative. And actually, it's easier to defeat Radio Personalities or Cable News Anchors if you have a full squad of 6 people fighting them. So again, what is the benefit of splitting up your squad into multiple parties? When you're a small group of Liberals in a location populated by hostile Conservatives, the LAST thing you'd need to do is split up and make it even easier for them to pick you off one by one.
So in summary, any amount of benefit from adding this feature does not outweigh the costs of how difficult it would be to implement and how it would unnecessarily complicate the code and make the program more likely to have errors and crash. At least that is my cost/benefit analysis (although I do admit that cost/benefit analysis is a Conservative notion, so you can discard it if you wish). However, speaking from a Liberal perspective, it would be great if we could implement every proposed feature, that would be fantastic in a Liberal utopia, and I wish it worked that way. This feature COULD be implemented, but there'd be quite a bit of difficulty involved, and I don't really see what the point of this feature is, I don't see WHY you would want to split up in the first place, what do you hope to achieve by splitting up?
In a Conservative world, Liberals gotta stick together to survive. Peace.