Very first Apple product:
First Gen Shuffle. 512MB of music. Used it for two-five months till this replaced it:
30GB iPod Video 5th Gen. A month after getting it, what happened? Oh yeah, the 5.5 Gen came out.
Very first Mac of my own. I used PCs before moving to the Mac.
2009 13" MBP. 2.26GHz, 2GB of RAM, 500GB HDD. Christmas present from the family. Certified refurbished. An AASP screwed it up so Apple replaced it with a 2.4GHz 2010 model which is still kicking. That was replaced by the most expensive Mac I have ordered new to date:
Early 2011 MBP 15". Completely CTO minus the RAM. 2.3GHz i7, 4GB of RAM, Glossy Hi-Res display, 128GB SSD (first one, ordered it from Apple because SSDs were uncharted territory for me and if something got messed up Apple would cover it). Awesome machine. It fell victim to Radeon-gate before the "Radeon-gate" term was coined. A month after I bought AppleCare and it had just kicked in, they decided to replace it after 5 lobos. Got my first Retina after that.