Hi Glide, I'm impressed with your home made sail! In regards to your question on which blocks (pulleys) to use, it would depend on how big your jib is. If you were to call the distance from the bottom of the front stay to the mast 100%, would the bottom of your jib be 135%, 150%? If its more than 110%, then I would keep it the way you have it in your first post. It is possible the "track" shown in that picture is too far aft, and the 110 block may be too far forward. But there may be other ways to improve upwind performance short of remounting hardware.
When I first raced my 23 years ago, all I had was the stock 110, and I remember the same frustration tacking upwind. There are so many things to adjust in sail and boat trim, lots of info online and in the previous posts here. A couple of things I was doing wrong that may help you:
-Mainsail twist: Being a fractional rig, the top of the main sees "fresher" or faster moving air. The bottom of the main should be close to center line but the top of the main should be not so close to the center line. To accomplish this twist, move the main traveler quite a bit to the upwind side of the boat. Check that your boom is not past center line. This will cause the downward force on the main to be less and allow the top part of the sail to twist out to leeward. To check how much to twist, install "tell tales" on the trailing edge (leech) of the main, in three or four places, especially in the upper area. You can use bits of yarn, thin nylon strips, or bits of old cassette tape. about 4 to 6 inches long. Adjust your traveler so the top of the main is full (not bagging or fluttering) and the telltales are all streaming aft. In really light air I often find the weight of the boom alone is too much downward force, and use a bit of topping lift to raise it.
-Boat list: In light air especially, a tilt to leeward will "pre-shape" the sails with the required curve to produce what the airplane folk call "lift". It may be necessary to put the wife/dog/beer on the side of the boat the sails are on.
-Even or forward keel: I have found too much weight aft makes the 23 slower. If the winds are light, maybe the crew would like to relax sitting on the coach top, leeward side, near the stays? Warn them when tacking. Dog or beer may fall off, don't risk that.
This is just a couple of the many tweaks to sailing, always changing with wind and conditions. It's part of the fun. Anyone, feel free to jump in if I've made errors here.
-Chris