After a week it is still frustrating for me. However, I have learn to adapt.
I place the watch on the bed with my wrist on top and then lift the smaller strap up and take the large strap over it to the third hole. I press the strap onto the pin and then tuck it under.
It still take one to three attempts.
The bed keeps me from dropping the watch (again).
It's the same for me. I've had my watch since launch day and I still find it frustrating and feel like if I'm not careful I'll end up dropping my watch on the floor.
I basically have to sit down and place the watch on the upper part of my leg with the back of the watch face up and then rest my right wrist on it. I then have to bring over the end with the pin and then overlap that with the other end and try and make the pin go through the right hole before tucking the excess in. It usually takes me several tries.
As much as I like the design of the band it's not practical at all to put on. I don't see that changing,