That's kinda why you should always play it , no confusion is there in terms of where or how to go .
We have a fully working objective marker and objective pinner for each girls telling exactly what you need to do to progress the quests.
Secondly , while you can get most of the girls in corrupted segments all at once.
Getting the girls that are clearly busy with their lives to be interested in you will require commitment regardless of how good the mc looks or acts
So if.. you were hoping to shag every girl being a pevert , yea no then I guess you shouldn't look into it.
If you want actual connections however and see why the girls are struggling in their lives , give it a go.
You can have multiple corruption girls at once , roughly 6/7 I believe but having romance is another thing.
Since you asked me three questions now let me ask you one , why would a girl who's perfectly fit with her life date you and then let another girl take her place after she's romantically in love with you?
If lust , sure harem makes sense but if it's love yeah not so much.
As for estimation of how many playthroughs , 2 if you're only doing sandbox ( one for commitment girls and one for harem girls) and 3 if you want to see the main story continue as well where you remain loyal.