I think Drago should stay with the Legions, I'm not quite sure at the moment since he should have conflicting responsibilities.
Like I said the hook with Tarsis is the no-tech thing, which leaves the Sith in the lurch without lightsabres. I can invisage the entire Lahara sector Legionary Force (whats left of it) hiding on Tarsis and using it as base. Since ships can land and take off and as soon as something leaves the planet it starts working again.
The reason you don't take tech there is incase the Tarsae capture it and then somehow get off Tarsis.
Flax will be going there in the Cantina next thread so you'll get a look at it anyway. Obviously I don't want to unravel the whole world now.
I'm not really happy with the time skip. 20 years is going to screw with the characters too much, I think. How about four or five smaller jumps.
If we do a twenty year skip Hal will just turn into his father.