TiVo is like a mini-fantasy island for men! I know at LEAST 15 guys who would sell their mother before their TiVo!!
Another idea is, if he has a lot of vhs tapes, or tapes a lot of shows, a combo dvd/vhs player/recorder would be a good idea, and can be under $100.
As for clothes, if he has multiple sizes, and they seem to be between a medium and large, get the large. If he seems insulted, tell him that you bought the large because of his huge shoulders!
Is he a sports geek? Not that I know anything about sports geeks
but they usually have favorite teams, and jerseys or other team paraphenalia are usually cool. I found an autographed jersey on ebay for under $30 - the jersey of mr. honeychile's favorite player! If you go this avenue, though, BE SURE you can authenticate the signature!