Just a few comments here because there have been a number of suggestions, and I appreciate that.
Damsels development is focused on polishing the existing product, and adding to the character storylines, not in large scale additions or big changes in the game mechanics.
People always want a larger roster of active adventurers. There are many things in the game that have been written around the current number, and there are UI reasons why it's nice to have them all fit on the right side of the screen as well. I'm not going to overhaul that part of the game and rebalance everything around it.
I'm not a fan of making people click extra times to confirm actions, particularly in ren'py when the "back" function is enabled. If you decide to do something, I assume you want to do it (or will use the back function if it was just a mis-click.) Right now I'm playing a bit of HPWU and the fact that it keeps asking me "Are you sure?" when I decide not to try to do something is driving me up a wall. The phrase "retire from adventuring" is used when moving a girl to a job, to indicate that they are not going to be adventurers anymore. The phrase "permanent bond" is used to describe concubinage and slavery, to indicate that those decisions are, well, permanent.
The pregnancy quest is entirely optional and offers nothing much in the way of benefits -- skip it if it doesn't float your boat. It's a good example of the sort of thing that has been added due to player suggestions. To my mind a whole bunch of girls naturally on birth control is awesome! All the goals were added to give players something to do who really wanted to keep playing after killing the lich king, and they are all totally optional. Don't do stuff you don't want to do!
New clothes aren't likely to happen. I love the idea, but practically -- new clothes would entail an expense of my part, since I don't download pirated versions of rendering assets, and one thing I found with pregnancy is that when a change occurs, people want it reflected in every render. Giving a girl new clothes means re-doing practically every render, and that's not going to happen. Giving several girls new clothes means doing it for every girl who gets new clothes. It's a lot of work and rendering time for a relatively small effect. I considered it for the branching choices available to Sorceresses and Priestesses, so that Fire and Ice mages would have different outfits, and decided it wasn't worth it. It's as much work as adding a whole new class.
Right now the clothing changes are indeed a progression. Each time you get a girl to take her clothes off, her sexuality increases. It wouldn't be impossible to make that a one time thing, and to let you move it back and forth once you've "unlocked" a level, I'd just have to rework the coding. So I'll think about doing that, and I probably will make it possible in 1.17. Dunno why you'd want to make a girl wear clothes, but like the pregnancy thing, to each their own.
Bottomless renders would require 3 renders per figure, or 48 renders total to make that happen. That's not impossible, as the rendering time for those are short. It could balloon to more, since I have an intention of making topless and naked kneeling and kissing renders for the figures. I think the additional kneeling and kissing (and maybe other) renders are probably better than adding a new clothing option. Also, unfortunately, some of the girls clothing options might not support bottomlessness in an attractive way -- they were all tested for toplessness before inclusion in the game, but I know I had to not use some outfits because there was no way to make just the right part of the outfit not appear in a render. So, great suggestion, but probably not going to implemented for practical reasons.