I had this idea once that I would pay $10 an hour to have a fairly new programmer sit next to me while writing freelance code and be a human sounding board, design helper, and companion since I work by myself from home. Not really pair programming as I'd be mostly running the show, but they'd be following the train of thought and offering suggestions. Could be a good job for a college student.
Would you be up for hiring someone for $10/hour?
I would pay $5/game to stream US professional sports a la carte from my laptop (for the games I want to watch).
I second that. Or something like Netflix but for sports (mostly interested in soccer and basketball), would easily pay 15$/month for that.
I would pay $100-200 for personalized travel planning services to remove the stress and uncertainty from planning a single-stop one-week trip; and $1000 for a multi-stop month-long trip.
I would pay $3/month for daily sentiment analysis of Amazon / Apple / Natural Gas / Gold on NY Times, WSJ, and Washington Times