John, I don't think that I am going to help solve your dilema, I have the same problem, deciding whether to wait, or to get something now. However, on the topic of what you want, and how good something is, let me tell you a short story.
This is a true story, that happened, or rather I saw, durring the summer, a year ago, about 2 minutes walk from my house in Toronto. I was crossing the street, when I car pulls up on the red light. it was a brand new corvette, driven by a young teenager, I'm guessing that he was 19, no more then 21. He thinks that he is 'all that'. Listeing to lound rap music, rocking his head, arm up on the driver's seat. We lock eyes for a second, and I get the impression that he is telling me 'haha, you wish you were me!' Now a corvette is a very nice car, and I wish I have one even though I can't drive yet, but here's the good part of the story, and remember this actually happened: Beside the corvette drives up a red Ferrari, driven by an older man, probably in his 40s. I don't exactly remember what Ferrari it was, It might even have been an F50, tho my memory is a bit hazy on that fact. The teenager in the Corvette looks over, and it was like his heart skipped a beat. His face was as pall as snow. He litterally, turned off his music, and sunk so low in his chair, that I could no longer see him. He couldn't blieve that the car beside him, was so much better then his. AS the light turned green, the Corvette was a little slower going off then the Ferrari, the kid was obviously still shaken after being showed up in such a way.
Now, I know that had nothing to do directly with photography, but the moral remains the same in both cases. No matter what you get, how much you spend, there will always be something better, that your equipement will look like crap compared to. in that moment you would do anything to have that better equipment, but you can't. All you can have is the knowledge, that one day, even that equipment will be outdone, will get old and will look bad compared to something newer and better.
The moral of all this: don't worry so much about the future, and if someone else's equipment will be better then yours or he got a better deal on it. Life's too short to wait, get the best that you can now, and enjoy it. If you simply save up your money waiting forever, you will die a very rich, lonely and sad man.
Carpa Diem, Stefan Tarnawsky