For the imperial stout I would go with a darker crystal malt than the cara-pils (say a blend of ~60 and ~120), a 1.104 beer will have plenty of body on its own, but the darker crystal/cara malts will add dark fruit and caramel flavors that will blend well with the dark malt. I would also use a yeast other than T-58 (which is Belgian-ish), say S-04, US-05, or Nottingham if you want to use dry yeast.
Barleywine looks good, although I'd probably drop the chocolate and roasted barley unless you want a darker barleywine. Some of the best English barleywines are nothing more than pale malt with a long boil for color. Some thought on the T-58, I'd switch to another strain.
Other than that just a few general tips on high gravity beers: pitch lots of yeast (2 packs of rehydrated dry should get it done), give it plenty of aeration at pitching, keep the fermentation temp towards the low end for the strain (but let it rise a bit towards the end), and give the beer plenty of time in primary and secondary before bottling.
Good luck, should be good beers to save for a few anniversaries to come.