Yoou gotta learn. Really.
Here's what works for me, and why:
1. Pedro levers. They're light, have a fine "hook" and work well. Don't break
2. Topeak Road Morph pump. Works like a floor pump so you don't need to hold the darn thing akwardly and it can generate real pressure, not just "get you home" pressure.
3. Don't go CO2. Your pump will never run out, and if you make an error, you just pump more.
4. Carry a tube, and also Rema patch kit for that 2nd flat. TRead the directions. Most new users put the patch on too soon after the glue.
5. A little pack of hand wipes can make you feel less grungy when you're finished.