i have played with all this stuff and have the same setup as yours on our current boat which is about to be trashed. The "ideal" situation is to have ball bearing stanchion blocks properly sized for your furling line. The current boat uses a mix of cheap alternatives. A crappy block attached to the toerail with a hose clamp in the bow, another just aft of that one attached to the deck, then deck mounted fairleads back to the cockpit, a single stanchion block and a turning block that has exactly the 270* as you described on your boat. The deck mounted bow block was installed with the wrong angle for the furling drum, therefore the second block was attached to the toerail to get that angle correct.

So, what is your line run through to get it aft? If ball bearing stanchion blocks I have nothing to add. if plastic bullseye fairleads, at the very least I would change those out to the ones with the SS inserts. If you want a nice and relatively inexpensive ballbearing stanchion block you can try the guys at Sailcare in Ford City. They carry the Viadana brand, made in Italy and looking 99% like any Harken unit you find. These stanchion mounted units do a couple of things. They are ball bearing so really efficiant, they also keep the line up off the deck and from laying in the rain water and general deck grime. There are also non-ballbearing units but why bother?