It should not surprise you that I begin with a disclaimer, but the value of any chip is subjective, and each person needs to decide the relative value of a chip for themselves.

But as far as guidelines go, here are my views as they relate to your questions:

1) All things being equal, I would not trade 5 $1 chips for 1 $5 chip. That is not to say, I wouldn't consider it under certain conditions. For example, I wouldn't have a problem trading 5 $1 chips from Illinois Joliet (or Las Vegas strip) where I (and regularly) do go, for a $5 chip that I want from someplace I am unlikely to be or go.

2) The only change I would suggest in this list is $1 chips should be valued at $2-$3. A current house chip from a strip casino is worth no more than a buck over face (IMO). The values are geared more to buying and selling chips, as opposed to trading. Applying rigid values in a trade situation isn't really ideal.

3) I can't say I object to the values you have listed for any of the chips posted. I can say if I was looking for a Bills chip, I would not pay $3 and postage, but some of the others are certainly more difficult to acquire.

These are solely my views, and are offered at the request of the original poster, I sincerely believe that this is an issue that will have many legitimate views. Ok I closed with a disclaimer also. I hope this helps.