Over the years I have become a hopeless softsynth addict. I am especially vulnerable to special offers. There are many synths I've bought which I will probably never use, some of which weren't even cheap.
Zebra and U-He
Out of curiosity I looked these up in my gmail history. I have criminally neglected this synth over the years, and only recently set myself the task of properly studying and using it. I do think it's a great leaning synth, since it covers a lot of bases, lets you see your signal routing visually, and can approximate a lot of different synths.
Zebra 2 is one of the first softsynths I bought: 10 Sept 2008. Then The Dark Zebra in 9 Dec 2012. Over the years I've pretty much completed my U-He collection (getting Bazille as a freebie with Bitwig 1, MFM2 and Uhbik quite early on, adding Diva, Hive 2 and Colour Copy and Twangstrom when NI had a 50% off promo, and then finally Filterscape and ACE when they had a 50% Black Friday sale).
Earliest plugins
The earliest plugins I bought were Stylus RMX, Korg Legacy, Absynth, and I think Kontakt 2. DAW-wise I started in Garageband, progressed to Reason 3, and then to Logic (first Logic Express, which gutted the built-in synths from Logic Pro, hence starting me on my softsynth journey). Then I moved out into a small place, didn't take my iMac with me, and moved to a laptop running Windows. So moved away to Reaper and after a little while Ableton 8, and later on Bitwig 1.
The trouble is, it's far easier to buy music software than to properly learn how to use something. I recall in interviews people like Armin saying that Logic's ES2 is all you need. I call my general weakness for technology my Technolust, things such as powerful workstations like the Z800, or bits of music software, and so on. But I guess an expensive softsynth habit is better than an expensive drug habit.