If its an extended stay or a special occasion, I try to investigate, before I arrive at the hotel, the different accomodations available at the property. I use the internet, including the property website, and including the Flyertalk forums, and I sometimes call the hotel, to inquire about special rooms, suites, views, "deluxe" or "superior" rooms, etc. It's much easier, armed with this information, to make specific requests at the front desk. You have some idea what to ask for, or what is being offered to you. I wouldn't, generally, do this for an overnight in, say, South Bend, but I might for a five night stay in London at the County Hall or Chancery Court. Of course, sometimes this might lead to disappointment, as you will know what you are missing on the occasions when you are told that the upgrade is unavailable. In the past year, or so, I have found as a platinum, that upgrades are frequently provided, although a specific request is sometimes necessary. Keep in mind, that sometimes an upgrade to a specific floor or view is more valuable than an upgrade to a suite. As to your comparison shopping question, while I generally don't do this, I have on occasion. I didn't get the impression that the staff was put off by the request.