I'm not sure I'm a fan of basing the system on consumable repair hammers, unless the rate of equipment degradation were decreased very significantly compared to the current beta. I wouldn't want to have to cart around dozens of hammers just to get through a long dungeon - that's maybe exaggerating a little, but not much, if you'd only get 1-5 uses out of one hammer.
Numbers can be changed.
Another idea, maybe better than a flat "repairs 20%, no matter how much durability the thing has":
Repair Hammers contain 300 charges. Each charge can repair 1 point of Durability. If you have Repair 1, you can use up 60 of the charges, leaving you with 240. With Repair 1, you cannot use a Repair Hammer which has 240 or fewer charges. "Not enough Repair."
Using charges 180-240 requires Repair 2.*
...
Repair 5 lets you use up charges 1-60 (after you use up them all, the thing breaks).
Yes, you'll have to carry around a few repair hammers. Too bad.
* The reason to count down instead of up is because of all the potential headaches that could ensue if you transferred partly-used repair hammers back and forth between people with different levels of repair. That sounds like it would take a lot of code to script and be buggy.
I think we're making some assumptions about the amount constant repair that's really going to be required. You might, for example, lose 5 durability over the course of a battle and have a range of 30 durability points between shifts in skill requirements. If that were the case, is expecting a player to do some checking on and maintenance on his gear once every 6 battles really that unreasonable?
I do think it's realistic to have a point where the problem (durability damage) exceeds ones skill to address (repair) it. At some point someone is going to run into something that is
Different weapons use different amounts of durability. As I said, a dagger uses 2 durability per attack.
Your approach may be realistic, but realism is not automatically the best way. That system is mostly punishing players for not micromanging all their equipment for all their party members after every battle. I think there are better ways to make points in Repair useful.
To make your system a bit fair, forget your zillion speech bubbles idea - by the time you see them, it could be too late for them to do any good. No, you need to be crystal clear where the "red line" for when you would be unable to repair things. If you moused over a dagger, you'd have to see "needs Repair 2 to repair below X durability" at the very least. NOT just if you have a repair hammer equipped - because you might not - but all the time.