My guess is, the reason you think Season 2 isn't as hot, is because the Devs have expanded the game with more routes. In Season 1, there was effectively only one route ( the only variation being whether Jeremy was alive or dead ). That mean't that the main corruption route predominated, and Deep was able to incorporate more scenes on that. In Season 2, more routes have been added, that follow a softer corruption path, and that means there is less time in each update, to pursue scenes on the main 'harder' corruption route. Also they've expanded the storyline, so they need to include a lot more cut scenes than they needed during the first season.
I've been following this game virtually from the beginning, and I've played both seasons dozens of times. Let's just say I'm probably it's Number 1 fan, and I think about it quite a lot. I don't think the scenes in Season 1 are that much better. I think a lot of people look back on Season 1 with fond memories, and remember that every update took Anna's corruption up a notch, but that was only possible because the game was so linear, all you could decide was whether she had sex or not. Now in Season 2, we have much more of a real choice, which will continue to grow and evolve, until at the end there will be several totally different versions of Anna.
Believe me, I understand the frustration of the slower development of Anna's corruption during Season 2. Although I play everything, I still favour the 'harder' corruption route that made up the bulk of Season 1, and at the time was probably the best content of it's type around, which is another reason why people probably look back so fondly at Season 1.
I think people have a perception that things have gone downhill since then, which isn't really accurate. The first porn scene and the first Bar scene in Chapter 2, in my opinion were both better than anything in Chapter 1. Also in Chapter 2 Anna has effectively become a prostitute, and seems perfectly ok with it, she's pretty much accepted Patrick and Jeremy using her as a fucktoy, and seems to get excited by having sex in riskier and riskier situations, where Andrew could easily discover her. She's now a Porn Star, could end up as a gang boss and now seems to be forming connections with some of the richest and most powerful people in Sun City. Her corruption has moved on massively. So there has been quite a lot of hot and hard corruption content in Chapter 2, but interspersed with somewhat softer content to develop the additional routes and a lot more cut scenes with no sex, to progress the expanded storyline. So it's definitely changed, but is it less hot? I don't think so.
And I firmly believe Deep and Awake are planning future scenes, that will blow everything in Chapter 1 out of the water. This is one of the longest running adult games ( it's now in it's eighth year ), and I fully expect it to be one of the very few that will last over 10 years. One thing you can be sure of, the Devs will want to end this game with a real big bang (literally).
Actually Anna hasn't fucked every man in the storyline (yet). But she's fucked a much much higher percentage of this games characters, than in any other comparable game. She is literally now the biggest slut in adult games, well at least in VN type photo-realistic games anyway, by some considerable margin. Until it was rebooted, Anne from 'The Adventurous Couple' was Number 1, but now she's playing catch-up again, and with all the new characters the Devs have introduced recently, all of whom Anna will likely fuck eventually, I think Anne will have to settle for the Number 2 position ( in any case she's not the game protagonist, so does it really count?)