One step at a time here. These cars are finicky and changes need to be made one at a time followed by confirmation that it worked OK.
I'm going to disagree with Earl here and say that you need to get the boost to be consistent whether you are running dump open or closed. So, I am thinking that a check valve type boost controller would be a good and cheap (by Buick standards) addition. Install it and make sure that the boost is the same whether you have the dump open or closed. If you have a decent chip, you should be able to run about 17 +/-1 PSI of boost WITH NO KNOCK. After you install the boost controller, start with it set to a low boost number (say 14 or 15 psi) and verify that it doesn't change with the dump open or closed. Then, slowly adjust it to increase boost, again confirming that it doesn't change with the dump open or closed. As soon as you see any knock, back off a PSI or two to be safe. Like I said, with good 93 octane gas and a decent chip, you should be around 17 psi give or take.
EDIT: Of course, check all of the hoses going to the wastegate solenoid, actuator, etc. first. Good call there. Although, the fact that boost changes with the dump open or closed makes me think the issue is somewhere else.
Once you get to this point and things are running consistently and reliably, then you can try more upgrades. First thing I would do is a different exhaust behind the downpipe, because your current exhaust with Flowmasters is apparently choking your dump-closed performance. Next would be injectors and chip, since your 36-lbers are probably going to be getting pushed to their limits if you run anything more than about 17 or 18 psi. Regarding spark plugs, I've been running NGK UR5's at a slightly tighter than stock gap for years.
With your combo, the only way you are going to see 11's is with alky or racing fuel, which will allow you to run over 20 psi of boost. Not going to get to 11's with 93-octane and your turbo/stock engine. See my signature to get an idea of what it took to get me deep into the 11's with a TA49 (basically the same as your TE44) and stock engine. You will also need good traction - a set of drag radials or slicks - to get there. But, remember, one step at a time. Get the boost under control first. Take your time, one step at a time. Make sure the car is running well between each step. Trust us on this.
Good Luck,