Need advice on replacing an old leaky roof

“I’d rather deal with a bit more hassle upfront than keep shelling out for patch jobs every year.”

That’s pretty much my take too. Complicated framing can be a pain, but if you get the right system and install it properly, you’re saving yourself a lot of future headaches. I’ve seen people try to cut corners and it just leads to weird leaks in places you’d never expect. Sometimes it’s worth biting the bullet and doing it right, even if the framing’s a puzzle. Just make sure whoever’s doing the work actually understands the quirks of your roof—seen too many “pros” get tripped up by odd angles.