An Atari ST 520 stfm. To 'help with my homework' not play Dungeon Master and Oids, oh no.
Paid for by doing a paper round every Saturday for about 8 or so months. Should have taken about a couple of hours every Saturday, but instead took about 3-4 hours, as my 4 year old brother decided that he should help me, and 4 year olds A: can't walk fast, B: often decide things like they want to put papers through basement letter boxes all on their own which leads to much convoluted hiding so you can't be seen watching if they are ok.
My first PC? 486DX 33 with a whopping 8 meg of ram and a 104 MB hard drive, which actually did greatly aid me with my degree (although I suspect anything with a spellchecker, and the ability to make words legible would have done)