I would suggest bagging the L1 on a motor deploy flight. Eliminate the learning curve/risk of the DD setup from the cert flight. Build it for DD but go with motor eject for the cert flight. I think I used a CTI H110 2-grain White motor for the cert flight...low and slow. It's not a bad idea to fly the same motors for the first DD flights so you can see what is happening at the events.
Start with one gram, expect that it will be pretty energetic. CTI uses 1.3 grams for the motor eject charge in their 38mm motors, that's not enough to hurt the DJ Jr. and enough to push out a pretty tightly packed chute in my experience. I have not tested the lower limit, but others who have told me that .75gr may be enough.
You hit it on the head - try to recreate the conditions as close as you can. Plug up the top of the motor casing with something and pack it exactly like you will at the field. Long motor tubes take up space, so maybe less powder is needed. Tightly stuffed parachute bundles - they might act as a piston when the charge is below, but the DD charge is on top and the shock cord needs to pull the package out of the tube. The DS Jr. was my first L1 project and my first DD project, and I figured that since it was strong as heck, I didn't need to get too cute with the "perfect" soft deployment charge, I just used ~1 gram top and bottom (since I think that is what Tim suggested) and let 'er rip. Never had an event failure.
And why should I, when there are so many other failures I can make.