Two fluid model of anthropics. The two different fluids are "probability" and "anthropic measure." Probabilities come from your information, and thus you can manipulate your probability by manipulating your information (e.g. by knowing you'll make more copies of yourself on the beach). Anthropic measure (magic reality fluid) measures what the reality is - it's like how an outside observer would see things. Anthropic measure is more properly possessed by states of the universe than by individual instances of you.
Thus a paradox. Even though you can make yourself expect (probability) to see a beach soon, it doesn't change the fact that you actually still have to sit through the cold (anthropic measure). Promising to copy yourself later doesn't actually change how much magic reality fluid the you sitting there in the cold has, so it doesn't "really" do anything.
I like your general approach, but I find the two fluid model a confusing way of describing your idea
For some time I've been pondering on a certain scenario, which I'll describe shortly. I hope you may help me find a satisfactory answer or at very least be as perplexed by this probabilistic question as me. Feel free to assign any reasonable a priori probabilities as you like. Here's the problem:
It's cold cold winter. Radiators are hardly working, but it's not why you're sitting so anxiously in your chair. The real reason is that tomorrow is your assigned upload (and damn, it's just one in million chance you're not gonna get it) and you just can't wait to leave your corporality behind. "Oh, I'm so sick of having a body, especially now. I'm freezing!" you think to yourself, "I wish I were already uploaded and could just pop myself off to a tropical island."
And now it strikes you. It's a weird solution, but it feels so appealing. You make a solemn oath (you'd say one in million chance you'd break it), that soon after upload you will simulate this exact moment thousand times simultaneously and when the clock strikes 11 AM, you're gonna be transposed to a Hawaiian beach, with a fancy drink in your hand.
It's 10:59 on a clock. What's the probability that you'd be in a tropical paradise in one minute?
And to make things more paradoxical: What would be said probability, if you wouldn't have made such an oath - just seconds ago?