To answer your question, I don't think any major rework has occurred, just little drips of new content in each successive update. Anal in the game is very limited in my experience BUT again I avoid Naomi, Blair, and Yona. Naomi could be a backdoor pirate (see what I did there?) for all I know - I stopped advancing her story real quick because early on I was doing the whole lift weights with Naomi path, and it did this scene where she squatted on the MC's face and went into all this graphic detail about how the putrid smell of her sweat and ass was overwhelming the MC and I gagged IRL and noped the fuck out of her whole storyline at that point. I actually think she is a cool character, I like her personality, I would love to shoot the shit with her and knock back some beers in real life, but she disgusts me sexually. Just my personal preference. And Blair and Yona? No clue what content they have, not interested so haven't pursued them.I like chubby characters and tomboys, but is more about choice, you don't like them, I do, I don't like slutty characters, other players do, is about giving a freedom of choice to the players rather than discussing which character is better, the concept of this game is amazing for a sandbox game but its really lineal with the progress.
I would love some anal-only if my list below this comment wasn't obvious enough. But in general, games that allow you to perform an action without being forced to do another in order to progress, speaks really well about how good is a game with sandbox and freedom. The dev has release updates that change existing content or is every update just new content?, the whole game needs to be reworked.
OT: have you checked out A Struggle with Sin? Lot of chubby characters and a lot of anal in that game, FYI. And it's pretty drawn out like you have to go through a lot of "oh holy shit it's so tight ahhh I can't take your big cock AHHHH" type shit along the way before you can just pound their ass. There are like a million anal scenes in that game. There's even a series of quests about getting them ass dildos and figuring out how to "craft" lube for it lol. (But most you can still force the issue and just do it the hard way without the lube also.)