Well, I'm still happy to provide feedback.
1) Making sex optional (---)
I'm still of the mind that it is Harem Hotel, not Wholesome-Family-Dinner Hotel. It's just a completely unnecessary monkey wrench in the entire development.
2) Objectives (---)
What to do in terms of further gameplay is I dare say never in question. Getting more money, advancing stories, that can be figured out by braindead chimpanzees. What to do to trigger the advancement of character stories (for example, how to trigger Moon level 1 event, to start her storyline) THAT'S causing the hangups, because that's often extraordinarily counter-intuitive. So no, the ways you described would be of no help whatsoever, even so far as it would be detrimental, because it would trick the player into thinking they did the right things to get X scene, and it would not achieve that.
3) Interactive Phone and Calendar (+)
That does indeed sound nice, I'm not really big on the whole "sending nudes" thing, I'm of the opinion that if I wish to see one nude, I'll go there and take off their clothes in person, but I'm not against it either, so I don't mind. The Calendar does look a tad... long tho. As in it takes ages to see someones birthday. But hey, unless you tie friendship events to it (like Ashleys), I'm sure it'll be fine.
4) Lounge Room (++)
Lounge on the 3rd floor is... well, I'm sorry, but bloody stupid. Lounges are on the ground floor typically for a reason, and that's precisely because 1) it's equally "inconvenient" for everyone, thus, a sort of neutral ground, and 2) it's the safest in terms of fire hazards, which are more present when it's in use. Considering that the hotel is already out in the middle of nowhere, I'm sure either buying 60+ square meters (or bald eagle screech per oil barrel, or whatever americans use) of land from the local council is not exactly a problem. In the 1800s in America land was literally given away for free on the condition that the new owner "improve" it somehow, so even just giving it away wouldn't be out of the ordinary for a developing continent. So just have the lounge be an extension of the ground floor (to the left in the screen I'd suggest).