I did a smash apa with galaxy and it came out tasting very similar to grape juice. I didn't enjoy it at all. Galaxy is best used with other hops in my opinion....
I buy all my specialty malts online and my base malts, hops and yeast at my lhbs. Lhbs doesn't have a great selection of malts yet otherwise I would buy everything there. It would cost quite a bit to ship a 55lb sack of two row....
Headys is a great beer, but not at 15$ a can. It usually sells for 8$ a can in restuarants and bars in northern vermont. It is almost always available in establishments, never in stores. It's good, but vermont has so many great beers!
I usually use 1/3rd more grain when I go no sparge. Set your mash calculator to "0" for sparge for your mash volume. I tried this method to save time. It didn't, as it took longer to heat the larger mash volume all at once. Good luck!
I know it's a homebrew cliche, but kegging saves so much time. Bottling was not a part of the hobby I enjoyed so I see it as a worthwhile investment. I only recently gave away all my bottles to a new homebrewer as I thought I might want to bottle some brews. I just use growlers now.
I find the grain bill to resemble a double ipa more than a barley wine. I would dump the sugar and bump up the Maris otter. Boil as long as you can for character. Just my 2 cents.
Having tried roasting 2 row several times, I have never gotten the flavour or colour I wanted. I find using either Maris otter or another specialty malt like biscuit gives you more of the flavour you might be looking for. It smells great though!