Overview

I believe that they way you have broken out the problem is completely correct. You need to distinguish the "Coin Flip" scenario, from the situation where the money is added to the envelope before the envelope is chosen

Not distinguishing those scenarios lies at the root of many people's confusion.

Problem 1

If you are flipping a coin to decide if either double your money or lose half, always play the game. Instead of double or nothing, it is double or lose some.

Problem 2

This is exactly the same as the coin flip scenario. The only difference is that the person picking the envelope flipped before giving you the first envelope. Note You Did Not Choose an Envelope!!!! You were given one envelope, and then given the choice to switch This is a subtle but important difference over problem 3, which affects the distribution of the priors

Problem 3

This is the classical setup to the two envelope problem. Here you are given the choice between the two envelopes. The most important points to realize are

• There is a maximum amount of money that can be in the any envelope. Because the person running the game has finite resources, or a finite amount they are willing to invest
• If you call the maximum money that could be in the envelope M, you are not equally likely to get any number between 0 and M. If you assume a random amount of money between 0 and M was put in the first envelope, and half of that for the second (or double, the math still works) If you open an envelope, you are 3 times as likely to see something less than M/2 than above M/2. (This is because half the time both envelopes will have less than M/2, and the other half the time 1 envelope will)
• Since there is not an even distribution, the 50% of the time you double, 50% of the time you cut in half doesn't apply
• When you work out the actual probabilities, you find the expected value of the first envelope is M/2, and the EV of the second envelope, switching or not is also M/2

Interestingly, if you can make some guess as to what the maximum money in the envelope can be, or if you can play the game multiple times, then you can benefit by switching, whenever you open an envelope less than M/2. I have simulated this two envelope scenario and find that if you have this outside information, on average you can do 1.25 as well as just always switching or never switching.