Hi stehansen,
Let's see 17 cypress coming down to 25 feet, all in one backyard.
Sound to me like we are making a hedge. Excellent, cypress make beautiful hedges, we have 30' cypress hedges coming out the bazoo here. Hack on them and they just get bushier, perfect hedge material.
When you top them out, in big pieces or small depending on your drop zone size, cut the "ears" out of your holding wood, otherwise they will strip the bark down.
Then tell the homeowner to feed them some high nitrogen fertilizer or do it yourself and charge him for it.
Make sure the owner understands he will need to water the hedge well, a run of soaker hose on a timer makes it a piece of piss.
Make sure the owner realizes he will need you back in a few months to shear the sides up nice and tight and that then he'll need you to come back and repeat on an annual basis. $$$ for you!
He's going to have one awesome hedge.
If we are not making a hedge, none of my advice applies.
RedlineIt