Nice Stuff Rel.
I am considering adding some of these for my home game (also in the Triangle

). One question, how about during a Short Rest? Do they just burn surges at 1/2 value instead? OR can then only be healed by a Cleric using his encounter powers (or Healing Word) during the short rest?
My party likes to (sometimes) do the 10 min rest or the "double-short" rest so that the cleric can use his powers to optimize the use of surges and then get them back for the next encounter.
I like the skills option, the milestones (but, admittedly, in a dungeon the 1 per 2 may still be in effect -- not sure yet), and I actually only pseudo-track XP and I am thinking of just leveling them up when I think they are ready. Since I am running
AoW converted for
4e, it will be easy to estimate this.
Rituals and Magic Items -- I have been using improvised and unique reagents for a while and will continue to do so. The old Phil Reed 101 series (3.x) had some good ones in there, or powering spells, making items, etc. I do like your Magic Item ideas. I would have special mundane items (like an heirloom blade, or dead father's ring) become magical in certain circumstances since 1e and I love the fact that you are trying to codify it.
Good stuff!