Is Glass Armor obtainable at level 1 in Solsthiem, and if so how much luck is involved with each method to find it?
You can find a pickaxe and mine malachite from the Glacial Cave or Nchardak, assuming you could survive there at level one. However you can't craft glass armor without the requisite perk, which requires 70 Smithing, which you can't really get without leveling up a few times.
There are very few fixed sources of glass armor; Northwatch Keep and the Thalmor Embassy have guaranteed Thalmor spawns, but they won't be wearing glass armor until you're level 36. They're in Skyrim anyhow, not Solsthiem. I don't think Solstheim has any fixed spawns of the armor or creatures that would wear the armor.
Your best bet for getting it as early as possible is probably to level only Smithing until you hit 70 (to keep your level as low as possible), taking the appropriate perks along the way, and then make a beeline for a malachite ore vein and craft the armor yourself.
Or to cheat.