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Only if your campaign is on a tight time limit, and assuming that you don't practice in the course of conducting your campaign. I imagine, for instance, riding from town to town would let you automatically gain skill points in ride. In a situation where your options for leveling up UMD are to...

Seems kind of odd to spend time creating a system where you gain skill points based on the in-game application of skills, and then shoot that system in the foot by either 1) introducing a means of automatically acquiring skill points, or 2) doing daily checks that represent a slower rate of...

Why don't you just use Chameleons?

How would this apply to skills that you might practice often, but use infrequently, such as Use Magic Device, Ride, and Swim?

Behold! https://www.youtube.com/watch?v=63Od-l4G1fA

So sort of like the orbs from Fable?

Oh, so that's what that button does.

Or a trinket worn about the neck that provides protection from evil mind controlling spells.

If you're under such oppressive rule, then I submit Fireball would be more useful.

Remove Disease

Beguiler

Let's be fair, games in which the population is composed of haphephobes aren't implausible given that most settings emulate the period in human history known to have borne witness to the plague.

And how does having someone reactivate the item periodically address that issue?

There's a good chance that if the wizard casts Detect Magic on you (spellcraft modifier of +7 at 1st level, success on a 9 or higher, assuming no other bonuses are in play), he knows that it's an illusion spell emanating from your head. In other words, that the hat you are wearing is disguising...

Off the top of my head: Detect Magic Spot check (You can see through a magical disguise.) Listen check (Sound of equipment is not affected by the glamer.) Will save due to interaction (Unless the character refrains from physical contact by all means possible -- no paying for things personally ...

I've always assumed that it activates and does not need to be reactivated every X minutes, since the purpose of the ring is to enhance stealth, and having to turn it back on regularly would be somewhat counterproductive. There's nothing explicitly forbidding it, or any feasible situations which...

Under what circumstances would it matter?

Maintain your friendship by engaging in non-competitive activities that will offer others the opportunity to cheat, and find a D&D group near you through use of the internet, or just start playing in an online campaign. You should never put up with people who are behaving badly out of...

He's cheating.

Honestly, the bonus on wisdom based skills alone is enough.