Wow, I didn't expect this amount of of feedback, this is incredible.
I plan on getting an aquarium bubbler for the oxygenation issue and definetly adding some nutrients as per your suggestion reverseapachemaster.
A guy in the forum here made a 20 or 25% barley wine I got to try at NHC a couple years ago and, considering the novelty, it was pretty good. I believe the trick is to start off high gravity and get the yeast going and continue feeding the yeast sugar and very high gravity wort and aeration. You will also need a yeast that can tolerate the high ABV as most brewers yeast can't go much above 12.
Anyway, good luck, it is definitely an advanced technique. I'll PM him for you and ask him to chime in.
Typically, I'd say throw all the sugars in the boil but for something this high, I agree that incremental feeding might be the way to go.
If you're using all that LME, I'd try to start with an initial wort that's extremely fermentable. Low mash temp for 90 minutes or so.
And, no I don't think you can go too dark. I have no idea how roasty it will be as no one knows whats in dark extract, but you can be too roasty. I think the bigger risk is too sweet with that much dark extract.
What did you mean by a "Low Mash Temp?" Should I wait until I get into All-Grain brewing to attempt this? And do I increase fermentability in my wort?
Re low mash temp, that would be for all-grain.
Re aeration, I think you would be better off with a mix stir rather than an aquarium bubbler. I haven't ever seen anything scientifically-based that indicates aquarium bubblers are a good way to aerate wort. You will have to use a vessel with a relatively wide mouth to use a mix stir like a bucket or big mouth bubbler.