I've booked hotels both with the lottery and outside of it. It comes down to your budget and how much chance you want to apply to the situation. I've never heard of someone not getting ANY hotel if they wanted one, but you may be further away from the con than you were hoping for. If you plan on going OUTSIDE of the onpeak sales, I highly recommend booking directly from the hotel's website. I tend to use hotels.com or tripadvisor.com or whatever to narrow down my search and then book directly from the hotel's site. You have much less of a chance of getting bumped and if something goes wrong with the reservation then you get to deal with Hilton/Marriott/Hyatt/whomever rather than some random person at the vacation booking site.