Although I agree with the majority of the posts here, I'm going to side a bit w/ the OP.

Being realistic I (and probably other FTers would be well) would be a bit cranky if I had even a bit of status w/ Marriott (or fill in the chain) & someone who PL'd who had no status got a better room than me & got their room after being told mine wasn't available yet. I might even stew a bit the first day if I had to push getting the room changed. But then - I'd let it go & enjoy the holiday.

And while Silver is like candy (ie, the Visa gets it for you), Marriott's # of nights required to get to Gold & Platinum is the toughest in the industry so a lot of folk are Silver who do stay at Marriotts (and might not have a M-Visa) who can't quite hit the Gold mark. Doesn't mean they're chopped liver.

Here's the part I don't understand - if an upgrade was part of the romance package, why didn't the OP mention that to the front desk clerk when s/he offered an upgrade for $100? Also, the fact that one was available for $100 means there were rooms & so the OP might reasonably expect to get something other than a solarium roof view. Having said that, the hotel did eventually do the right thing.

As others have mentioned, the hassle of getting the correct room really is the only legit complaint you have. The rest of your letter/points are irrelevant.

You probably don't want to hear this, but let it go. You've spent enough negative energy on the issue & life's just too short. You did get your upgraded room eventually. If you do decide to write again, focus only on that & your disappointment that your earlier email wasn't acknowledged.

Re: whether to go for 8 more nights/Gold status, you have to make the decision on whether it's worth it to you to do so given your stay patterns. Gold will get you more upgrades (no suites)/access to executive lounges - ie, you'll see more bennies than simply Silver.

Re: NYC. Someone else has addressed the various programs being dif, so I won't. But NYC is a popular destination & rack room rates are through the roof (at ALL chains). So while disappointing, not totally suprised standard awards aren't available. Also depending on when you want to go, some times are busier than others. There's a thread right now in the Hilton forum that due to some conferences, etc, room rates are $700/night at properties. And the weeks btwn Turkey Day & Xmas are always high.

Welcome to FT, btw.

Cheers.