Hey! So I'll be the person to respond to this since I guess it's more appropriate given I'm more informed than my Divisional Staff simply because I'm more aware of what's going on in the community.
To start off, Jailbreak was revived I believe in ~August 2020. A lot of people came back (including myself) and hadn't played JB in multiple years as it had been dead previously. Everyone was super stoked to see JB alive and well again and so we had like half a year where we had max pop almost every night.
Multiple people (including myself) just started off as a normal player and grinded JB to the point to where we were considered for mod, then global mod, then staff, and so forth.
While I thoroughly enjoy JB, I will acknowledge that I have burnt out to the extent that I have debated stepping down for about a month now. I have tried over the past month or so to get JB populated whenever I'm available in the evening and it seems that the drive and dedication to popping JB just isn't there anymore. This and some changes with how JB functions such as being able to purchase rep has really changed the mentality a lot of players had regarding JB. Using myself as an example, when JB first revived it seemed like the competition for gangs had redeveloped as they wiped all of the gang database and reset everyone. It turned into a year long competition to see which gang would rise to the top and win the "Gang war" that developed naturally in JB. After the rep shop came out there was no point in grinding JB or AFKing in the server, because think about it- you get like ~3 rep every 5 minutes for spectating in JB (I could be a little off- I haven't checked the actual number in a bit). Using that estimate you get around 36 rep a hour, and 864 rep a day. In the shop that equates to ~$1.30. So in a hour, you could get a dollar and thirty cents worth of rep. Why would you AFK grind when you can just go buy rep? The rep shop basically eliminated the eagerness to grind rep by AFKing in the server, and to get to my point, this effictively killed like 8-15 people spectating every day. That REALLY hurts our server population because when you look at the server list, it counts spectators in the total pop. So even at 4am, you would see our server with around 10 people on, which would entice people to join the server.
Moving on from that point, another thing that I think changed my will to play would be how the JB environment felt after a year of playing. In the beginning there were TONS of old players who knew how to lead and were experienced in the "roleplay" aspect of JB. They were knowledgable about the rules and how to lead days or rebel well. This added a lot of spice and exciting moments into the gameplay of JB. Over time, what always happens is people grow out of specific things- in this case, Jailbreak. Over the year we lost a lot of great players who made (in my opinion) jailbreak more enjoyable. That was a major hit to our population because they were the main people leading days as well. A big contributor to our lack of server pop is the lack of people wanting to lead days in JB. I personally enjoy leading for about 2-3 hours, but then I like to relax on T and rebel. This is fine if you have 6 people who want to do that, but when you only have 1-2 it becomes more complicated, because then you have to rely on those two people to carry the CT side in the leading aspect, which burns them out way faster than when they can just lead for some time and then vibe on T. Another issue was our general lack of CT players. Jailbreak is enjoyable because the 1:2 ratio that's implemented. This however, is not enforced in terms of forcing an equal CT to T ratio. The 2:1 T to CT ratio is enforced, but not vice versa. What this means that while you can have 30 T's and only 15 CT's, you could also have 30 T's and like 8 CT's, which, is most of the time going to result in the CT side getting demolished, and people not wanting to play CT, and with no CT's you have no JB.
To continue on, let me state that I am in no way defending the CS:GO Leadership right now. We are all burnt out, and we have a severe lack of drive (if any) to populate Jailbreak right now. I'm unsure what Gaming+ wants to do about this, as I've made it clear that we've felt that way for over 3 months now.
With that being said I'm hoping that something will be worked out for JB sometime soon, because while I'm burnt out, I still want to see JB succeed because of how enjoyable it is and how many hours I've spent relaxing on it.
Thats just my two-cents. If you have any questions or want me to elaborate further please ask. I love JB and I'm sad I'm this burnt out, but there's nothing I can do about it other than take a break.