Firstly, I'm not necessarily convinced that simulating a person necessarily results in consciousness, but that is largely irrelevant to this problem, as we can simply pretend that you are going to erase your memory 1000 times.
If you are going to simulate yourself 1000 times, then the chance, from your perspective, of being transported to Hawaii is 1000/1001. This calculation is correct, but it isn't a paradox. Deciding to simulate yourself doesn't change what will happen, there isn't an objective probability that jumps from near 0 to 1000/1001. The 0 was produced under a model where you had no tendency to simulate this moment and the 1000/1001 was produced under a model where you are almost certain to simulate this moment. If an observer (with the same information you had at the start) could perfectly predict that you would make this decision to simulate, then they would report the 1000/1001 odds both before and after the decision. If they had 50% belief that you would make this decision before, then this would result in approx. 500/1001 odds before.
So, what is the paradox? If it is that you seem to be able to "warp" reality and so that you are almost certainly about to teleport to Hawaii, my answer explains that, if you are about to teleport, then it was always going to happen anyway. The simulation was already set up.
Or are you trying to make an anthropic argument? That if you make such a decision and then don't appear in Hawaii that it is highly unlikely that you will be uploaded at some point? This is the sleeping beauty problem. I don't 100% understand this yet.
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?