My first console was the Sega Master system master system and since then I bought the following;
Sega cd,snes,dreamcast,nomad,gameboy,gameboy advance,gameboy sp,ds,dsi xl,3ds xl,ps1,ps2,ps3,xbox,xb360,psp,gamecube & the wii.
I have to say that the most surprisingly fun console I have had over that period is the Playstation Vita. If you got it early on as I did and had the playstation plus membership you got to download tonnes of free games including indie games and got deals on PS1 and PS2 games that looked perfect on a portable system.
If you get a chance to buy the original OLED version you won't be disappointed. There are a lot of youtube videos listing the great games on the Vita. I even bought the playstation TV so I can play most of the games on my bedroom TV.