^^ I would recommend against moving hotels after two nights, it'll just be a pain in the butt. You can always reutrn another time and stay at a fancier place if you want.
You will also want to make sure of the resort fees when booking, you could very well have to pay them at check inn as I don't think the booking sites include them, nor do the flight/ hotel packages you can book. While you are there pick up a Ceasers and an M Life rewards cards, these are the ways to book rooms in the future.
The outlet malls are not that ####ty, they are however over rated IMO and the pricing isn't great, especially at 22% exchange. Planet Hollywood (Miracle Mile) and the Fashion show mall have good stores/ selection etc,, but not the best prices.
The pools are not heated though you should still be okay as it'll still be qutie warm the first week of October. And staying on the strip gets expensive; morning coffee, meals drinks and snacks add up fast, you will spend more on food then you expect to.
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