Come on over to my camp, I am going to be sewing on some ot the Velcro to my wind panels this week, possibly this Tuesday afternoon. I will most likely, if it is too sticky, apply some wax to the needle and the thread. I have a small container of soft microcrystiline wax. But I also have a tube of pure silicone grease. Of course I can always hand stitch but of course it is much slower to do by hand.
I did get one of the sewing awls for lock stitching from the leather store by Dorothy and Totos ice cream. . Putting velcro onto the tent wall won't work with a machine unless you take out the tent framing pieces. The hand awl mehod would go much easier with the two partnering up one person on the inside the other on the outside. You helping with mine and me helping with you with yours. video link for how those stitching awls work. Very handy for this kind of work on canvas.