Am I Becoming a High Maintenance Traveler?

I'd like to think I'm a savvy traveler - I'm not easily stressed and I can usually handle whatever is thrown at me, whether it's a pesky cancelled flight or a rogue gate agent who doesn't know the rules of the game. My frequent travel entitles me to top status on Delta and with Hyatt and Starwood and some others like Hertz, all who treat me very well on a consistent basis. In fact, I think I've been treated so well, I'm starting to think it's warping my sense of reality. This past weekend I had a couple small travel snafus and I'm trying to figure out if they were really service failures or simply me expecting too much out of travel.

It all happened this past weekend when I had to be in Atlantic City Saturday night. Not in the mood for public transit, I used 500 Hertz points for a full-size weekend day rental (saving me $70) and used a corporate rate to stay at The Chelsea hotel - a renovated boutique hotel. Naturally, as a points addict, I tried staying at the Sheraton or Marriott, but they all had two night minimums and 24 hours is the absolute maximum time I can stand Atlantic City (and to be honest, I'd be happy if I never went again).

The first incident happened when I picked up my rental car from the Manhattan Morton Street Hertz Local Edition. The friendly agent gave me my keys and I realized it was a Corolla - which is not a full-size car. When I asked her for a full-size, she simply replied, "Sorry, we don't have any." I asked for any other type of car since I'm 6'7" and I really don't fit well in compact cars, but she refused saying they were low on inventory.

I don't doubt that they were low on cars considering it was a holiday weekend, but there are a bunch of Hertz locations in NYC and they could have gotten a full-size from another branch, or even called me before I arrived and told me to simply go to a different location. However, I was running late and traipsing around Manhattan wasn't an option. Seeing no other choice, I asked for a voucher and without hesitation she gave me one for $25. Honestly, I would have much rather just had what I ordered, but I took it and went on my way - cramped in my lipstick red Corolla.

After an uneventful drive through New Jersey, I got to the Chelsea Hotel with little time to spare. At check-in, I was told they were all out of premium rooms with king-size beds (what I reserved), so they'd give me two queen beds in the older tower - as if that was an equal exchange. I pushed back asking for what I reserved, but the front desk agent snidely replied, "We are busy tonight and since you are checking in at 7pm, we've already given out all of our premier king beds, so sorry, but that's all we have." Not satisfied with that answer, I asked for a room upgrade and he went to ask his manager. No dice. I then asked for free drinks or money off my room rate (if I was staying at a chain hotel I would have angled for points) and he went back again to ask his manager. This time he offered me $25 at the bar. Not having time to play this game, I took it and went to my room. Coincidentally, as I was going through my ordeal, a couple of harried guests approached the front desk - apparently they had been given keys to a room that was already occupied. That's only ever happened to me once (at the Sheraton Phoenix when it first opened), but shouted of poor management of the hotel.

As an aside, the hotel was pretty dingy and I definitely wouldn't recommend it. When we got to the elevator, the door only opened 1/4 of the way so we had to push it open in order to use it. When we got to our floor, not all of the rooms were numbered, so we had to try a couple doors until we got the right one. The room was fine, but definitely old school - loud heater unit and tiny shower with weak water pressure. The highlight of the hotel was the diner/bar in the lobby, which actually had decent drinks and food.

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But back to the point of this post, in the end I got $50 off my travels, but I think I was more than $50 worth of annoyed. But what do you think? Am I being high maintenance or should I have fought harder to get what I actually reserved? As a small business owner, I can't imagine not providing my clients with exactly what they paid for. If it just wasn't possible, my instinct is to be proactive about reaccomodation. I don't think it should be any different for travel providers, though is my sense of entitlement skewed because I'm normally pampered and upgraded instead of ignored and downgraded?
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