As one of the guilty folks and also a relative newb I'll take a stab at an answer.
My first springer was a Whisper. THEN I found out about the magic golden trigger. It kinda miffed me about having to buy it, but when I got it, saw the results, I didn't mind the price. I thought that the money I spent on the Whisper, trigger, and the Leapers Scope and nice mounts was a lot of money. However, that gun hits everything it shoots at!
The next gun I got was a 350 magnum. Now I wasn't ready for that gun. However now that I'm used to it, it shoots like a dream and was worth every penny I spent on it. So then I have basically two medium priced guns.
After that I went on a binge of cheaper guns. Why? Well if I really needed to hit something I could use the other two

. I bought a cheap refurb Air Hawk, which to be honest, has been a disaster. I've spent as much or more money on it than I spent on the Whisper. Between new springs, MM tune, etc, I have a lot of money in that gun. While it is better, I wish I had spent the money to get a better base gun like a "real" 34.
The next few guns are all AR1000 clones. I've learned to take them apart with varying results. However I like them and like how hard they hit as I like magnum guns.
If I had to do it over again, I'd probably just own three guns; my 350, a 34, and I want a Beeman R-9 or a Cometa. I don't regret the money I've spent on cheaper guns as I've learned a lot about what I like and what I would do in the future. My TF 89 is a great shooter and I don't have much money at all in it. The gun I regret the most is the Air Hawk. I've spent too much money on it with little results.