Can you flash replacement windows with existing siding?
Our house, which was built in '93, doesn't have flashing on any of the double-hung wood windows - they're just sitting in the rough opening with 'some' insulation stuffed around the sides. The builder only installed a 'wood' drip cap that I constantly paint (along with the sills), which still seem to rot on me! Knowing what I know now about flashing and how windows should be properly installed, I'm hesitant to just install replacement windows. I mean, isn't that like a half-finished job... new window and still no flashing?
Ideally, I would replace the crappy LP siding that is deteriorating, Tyvek the house and install new windows at the same time... but that would be very expensive since I have so many windows on the back side of the house.
So here's my questions:
1) Can I 'carefully' pry the LP siding away long enough to properly install and flash new construction windows?
2) If I can't install new windows without destroying the siding, can I go with replacement windows now, then later on have those windows flashed somehow when we install hardiplank in the future?
3) or do you guys think replacement windows are acceptable, and I just forget about the idea of ever properly installing/flashing windows in this house?
Hope this all makes sense.