Well, I'm not good on rudder shape questions so will pass on that one.
In general, place your jibsheet block so when close-hauled, all the way in, the angle of the sheet from block and mythically continued forward and upward, intersects the headstay and jib luff (same thing really) about halfway up the jib luff, or maybe 5 to 10 degrees "higher up" than mid-way.
Now I'm going to assume the "lead" of the sheet from the block to the winch drum is okay. It seems you have a how-to-wrap-and-winch question, and it's likely you need to keep it to two wraps initially while the sail is easily trimmed (meaning not full of wind yet) and the "new" sheet is still sort of slack or at least not carrying much load yet, and the jib not "filled" completely yet. Slack is easy on your arms, but it's also the friend of winch overrides, it's just too hard to keep 4 wraps alongside each other rather than on top of each other.
Once you have heaved in what you can by hand with two wraps (no handle yet) while you have a little slack and lighter load, THEN once you begin to get the heavier load, add the 3rd and 4th wraps stick the handle in, and crank away with one hand and the other tailing (pulling the sheet enough to keep friction on the winch drum). Or, if the force is strong (as Darth Vader would say), then hand the sheet to someone else to tail and use two gorilla hands on the handle. With a heavier load from the jib (and assuming the lead-angle from block to winch is good), this tension will tend to keep all 3 or 4 wraps in place on the drum.
The double wrap and pull with hands is what I was doing and it worked out good, but obviously you can't trim the sails hard with your hands. What do you mean by the lead of the sheet being okay? Here is a picture from the manual that shows the sheet lines...
This may sound like a lot to remember but it becomes second-nature real fast.
And yeah, in heavy air upwind, you don't want to sent anyone to leeward on a lightweight boat. So take maybe one, or two max, wraps on leeward winch, then take it up to windward winch, a couple of wraps there, and crankity-crank while you are all up on the windward rail. You need fairly long sheets for this.
So when you run the sheet through both winches you still need to wrap it at least once on the leeward winch then a couple times on the windward winch? I have plenty sheet length so this will not be an issue.
These are excellent first-sail questions! Keep 'em coming and best of luck.