LAST EDIT: While I'm here, thought I'd drop a suggestion in, the Wood Elf Shadow Play racial is really great, but perhaps a little imbalanced, it might be nice to consider changing it to Chameleon of mabey 25-75%. That way it would retain Wood Elves ability to blend in without meaning that someone right in your face can't see you.
That power is based on this excerpt from the Pocket Guide to the Empire:
For a brief time the Colovian armies used Wood Elf archers, as in the War of Rihad two years past. The Bosmer proved to be too undisciplined and prone to desertion for further use. They would sometimes walk into the shade of a single tree and vanish. Their forest-coupling skills are remarkable. The title of their most famous poem, the Meh Ayleidion, means "The One Thousand Benefits of Hiding."Total invisibility, even directly adjacent, seemed appropriate. The stiff immobility requirements and slight cooldown on re-activation are intended to balance it... if you've got playtest results suggesting that it's still a little broken let me know, but the current flavor is intended, even if it seems a little fantastic.

I'm surprised you had to hard-edit TRAP to get Robert's to work... it seems like the kind of thing Bash should be good for. At some point I need to get firsthand knowledge of that program so I can tag things appropriately. :spotted owl:
However, in the tutorial dungeon my inventory always showed the weight of a single coin was no matter how much gold (septims since i used the rename option in the ini) I had picked up. This also continued into the world at large.
Your actual encumbrance is being adjusted correctly. The reason you see only the weight of a single coin is the same as the reason you see only the weight of a single arrow, it's just how Oblivion displays stacks. The reason it's done this way, instead of having a single item which gets edited to have the total weight of all your gold, is to allow you to drop any number of coins through the normal inventory method rather than needing a separate user interface mod for that.
Speaking of a user interface mod, though: I bet one could be created which shows the total weight (and value) for stacks, much like Major Jim's shows base and effective skills/attributes separately. (No, I'm not volunteering.

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Well, I tried resting some more, slept for a week straight I think, and the power still wouldn't reactivate. :/ Anyone have any idea why this might be?
Unless you're using Tekuromoto's Time Manager, I have no idea
why this would happen. (And if you are, it would be a previously-undetected bug. That's just the only mod I can think of which plays with recharge times.) However, it should be fixable by changing your birthsign to something else, then back again.
Edit: For the record I'm taking a bit of a break. Have been for a week and a half already, in fact (so obviously I'm still checking in). I've been spending too much time sitting alone in a dark room; time to lose some weight and engage in non-virtual social contact. All those boring necessities of health and sanity, y'know?