Re: reef line set up
Yes, you will get a purchase of 2:1 with that system.
Smooth running line helps a lot when going around a fixed cringle. I use bare Amsteel for that portion of my reefing line (it is spliced to double braid for the portion that goes through the clutch and around the winch). You could also use a line (like Warpspeed) that is strippable with a dyneema core if you didn't want to do the splice. Dyneema/Amsteel is more flexible and more slippery than regular line, and it's low stretch properties make it a good choice for reefing lines.
1986 Pearson 28-2 "Elena"