The first device I hacked was an iPod 3rd generation, lmao. I then started to hack my Wii, which became an awesome experience for me knowing you could play almost all Nintendo games to emulators/USB loaders.
It was a pretty magical experience watching a toy transform into a pocket computer using just a cheap little piece of plastic called an R4. Been hooked on modding ever since.
Forgot in my post but just remembered I actually got a PSP 1001 already on CFW from Ebay (which was against their rules but I got away with it) for $50 I think with charger and 8 gb official sony memory card. It was on 5.xx something though and I later updated it to 6.60 and I bought a 32 gb micro sd adapter with 2 16 gb micro sd cards.
Capabilities unlock on a 3 months old Nokia 6120C in 2008, iirc
(pretty funny since nowadays when I want to buy an Android phone, I go to the stores in my area, look at what they have at a reasonable = under 200 price, then compare which custom roms do they have)
Around that time I also had a DS with an original R4, but who didn't considering you could buy them at any electronics fair in Italy back then