Guys, I have to jump in here since I really believe that this story is a typical "one thing leads to another" thing, in the way of "one word at the right time and the right tone will get you further, while the wrong tone might stop you instantly".

Lets see if you can catch my drift.

Now, first of all, Orbx runs a business which is lead by John, he's the CEO, but also a dev there. So he will always have to achieve a fine trimmed balance of money coming in and customers being happy about not too high prices and great service.
Sounds like a normal description, huh? Well, it certainly is, but, as we all know, not all companies around achieve this goal. Orbx, in my eyes, does. CS too, if anyone is asking.  :)

Back then, I was wondering about the limited time for V1 buyers to upgrade very, very inexpensively to V2 too. You can bet I wasn't smiling about this business aspect, but I recognized the emails, the forum announcements and the large banners at e. g. flight sim store (FSS) and the Orbx forums which clearly showed all terms and conditions, so I was ok.
I would speak about a very "loud" advertisement of the whole thing, so my assumption is that you've really missed some information there. Sometimes, this happens of course.

When you look at their current update and upgrade policy, you'll see that they are back to more customer friendly ways, offering patches for free, which not only fix problems but enhance a large range of their famous airports.
Check their site for details and enjoy e. g. all the new poepleflow stuff, it's great and free!

Last issue. I spoke about "tone" in the first paragraph. What I assumed there was that you might not have caught the right one to convince John.
As said, he's a business man, for sure, but he's also a guy which takes support very serious. First of all, he surely is a human being, so maybe the attempt to demand a discount instead of politely asking for it drove him to the decision that he can't help you.
The company defines the time limits there, not the customer, that's our world today. No one has to like this, but at least be aware of it.

Orbx is the only company I know so far which even warns people about their own products. They have a thread running, concerning the version 1 of the airport, which clearly stresses the need for a decent system.
Now, while V1 wasn't charming on every hardware around, the V2 really is a new product in case of the looks and especially the performance, so the 2.0 sign is well earned there.
Personally, I'd even accepted a nearly full new price there and, personally too, I think that, from a closer look, nobody will see Orbx as a company to warn other guys about.

As said, I think that the attempt from the FSS guy (could have been Jay, he's also active in the Orbx forums) to forward you to John showed this customer friendly way of operation. They didn't reject you instantly, but forwarded you to the CEO.
Now, starting a thread about one dev in another dev's forums might explain my thinking about the wrong tone and approach from your side when "asking" for an out of the rule discount.  :-?
This is just a very personal viewpoint of mine and I don't have the slightest idea what was spoken between both sides of course.

I don't know John or Jay personally and I'm in no way related to Orbx. I'm just around their forums too (catching some tone, so to say), bought tons of their products and already had some support issues running which all went fine and weren't always of an easy nature.
So I might be biased in a way.
I could warn you about some companies in the business, but I wouldn't do this in another dev's forums and I also would be aware that things happening between me and the company will not always, if ever, align with the experiences of other people. As an outcome, I don't warn people about any (so far).