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At first glance, nothing looks awry in this adjustment area, very solid not sloppy and set screws intact and tight. Is the pulley between the flywheel and housing another place of adjusting?

Wizcrafts, the timing definitely seems to be off. I'll adjust accordingly.

Wizcrafts. After further review I see I was wrong about the thread being picked up. I believe this is just excess thread from the top with loops that never were grabbed by the shuttle point. I found a seasoned local resource that may visit and give some on-hand tips. I'll keep you posted

Wizcrafts, I was able to measure the foot play front to back and wound up with a 1/32" measurement. Luckily, the bottom thread WAS picked up after I placed the better bobbin in place. See initial images of a sew on 3/16" soft deer hide.

Wizcrafts, I'll check this in a day or so. I assume the "slop" I'm looking for would be lateral in any direction of the foot? Also, I have seen that some feet have toes that are equal length, and others with a long toe and shorter one, reason?

Wizcrafts, the shuttle driver has a measured play of 1/16" back and forth. Hopefully this is acceptable.

Also, some images of the shuttle mounting area.

Wzcrafts, a picture is worth 1000 words, so here are a few that will clearly show what I'm dealing with. I threaded the machine tonight with #69 bonded thread (top and bottom) and mounted a #18 needle, hoping to get the top thread to pick up the bottom thread. Well....it did not pick up. After looking at each shuttle closely, I discovered the one I was using has a worn point. If you look at the marked up images you will see what I am referring to. My next plan is to remove a good spring from a bad point shuttle and place it on the best of the three and see what happens next. Unfortunately I only have these three shuttles which came with the machine and will need to purchase some new virgin ones.

Wizcrafts, thanks for setting me straight on this topic, the guidance and information is much appreciated. I was able to hit Hobby Lobby this evening and picked up some #69 bonded thread and a pack of #18 needles. I'll thread the machine and see what happens after some tests.

Wizcrafts, per your needle guidance. Will these needles (135x16 leather point and 135x17 round point) be acceptable with #138 T135 Bonded Nylon Thread? I saw this thread recommended a few times but know there are other options, just making sure I'm "pairing" correctly.

Understood, thank you. Also, regarding needles, plenty of info on gauge, but what is the ideal overall length? (Assuming I'm landing it against the 2nd set screw and not beyond).

Wizcrafts, thanks for the quick reply. So what I'm hearing, is that whether the thread is laying over the side, or up through the needle hole, I should get the same result?

Thankful to have been accepted into the Leatherworker forum. This is my first post and a question for all the seasoned leatherwork sewing machine users. I picked up this 1912 Singer 29-4 a few weeks ago and have it just about ready for use. While I do have a copy of the original users manual, I'm perplexed at what little info I can find about the needle plate. There is a hole just next to the needle passage hole (see image). Does the bobbin thread pass upward through this hole before commencing sewing? The Singer manual only states to lay the thread as shown and zero mention of this hole. I have seen videos online where the bobbin thread appears to come up and out of this hole. Any input would be appreciated.