Hobbies?

[FlyingClayDisk]

Yes drill press. I use metal HHS-G drills for that, I done the big cuff inserts with it too. A few years ago when I did not have the old Singer, I did it like you, drilling and then use a thread needle and pliers and did it by hand. Metal finger caps is a must for that. Of course there are special leather needles for just that, but I went with what I had. 

I did not handle Cordura yet, but if it's similar to heavy duty jeans, forget the normal needles and a standard sewing machine will have a hard time too. Don't forget it's also about transporting the material away from the needle. If that does not work, you're setup for failure / bad results.

With such old sewing machines like the Singer, it's all about the flow. I guess you talk about pedal powered? It takes a while to get into it. Best technique is to putt the whole foot on the pedal and never touch ground with the foot. Press down and let it come up alone by only lifting the foot. Some allow you to bring it up with the foot, by design or accident. They really do not like turning backwards, the threads get tangled up, runs out of the thread guards and so on.

Lol I think we had this exact conversation a while ago, it feels so familiar.

Cordura is the heavy nylon fabric that they make backpacks out of (or used to anyway, now a lot of them are made with much cheaper and thinner material).  It comes in different grades which equate to the thickness, and they also have grades which are treated with waterproofing coating to weatherproof it even further than it already is