OK, did my first run as a virgin (but still eros level 2 because I got bored of not having access to stuff) on Severe, and this was pretty fun.
There is definitely a moment when you arrive at like d40 and realise there is nothing to do anymore and you just timeskip to the next event, though.
Hardest boss was by far the dragon (extreme second fight), I had to wait until d100 to get skill unlocked for me to feel good about beating it. I could probably have done it without, but judgement made the three bomb phase trivial. Second hardest was the highest difficulty of the elite boss fight in the pomona church. It was somewhat tricky to make sure I had constant debuff immunity until it died (once again judgement came in clutch). Ueil was kinda a joke tbh, he died too fast for me to even think about using the new S skill.
Best "early" grinding spot is the orc elite double boss, it is 30-40k exp with training/adventurer. Then the Golsh elite boss is better. Pomono church mobs also give you a crap load and just folds to explosion, but I was wary of, well, not having enough energy to finish the dungeon.
Btw, you can definitely get the house in the noble district as a virgin, just can't sleep there or the freeloader will rape Alcy. Having said house does give access to a lot of good ASI. You also get two planet core (one from wriggle dungeon, one from star pieces), so you can get both Supernova DC and then Master III fairly easily.
it should just be a presentation bug. most "things are done in x days" are locked to specific days, not "day from now". So day 60, day 80, etc.