Not sure. Feels like Open Source in this case might cause more issue than it's worth. Too many cooks in the kitchen sort of deal.Somebody tried: Something Trainer
Would a Ren'Py remake have more chances to succeed if it was an open source project?
Speaking of ST, it looks like it's trying to do a bit too much, too different, too fast.
With a Ren'Py port, there's always the temptation of 'doing things different and better', but I'd rather just see a 1-to-1 stable transition to Ren'Py first, warts and all (definitely not the spaghetti code though).
Once you've built a solid foundation, then you can start thinking about improvement and changes - getting rid of the grind, making the bordello content optional/whatever.