Question
We live in upstate NY. The second story of our house extends about three feet beyond the ground floor, creating a virtual dead space along the foundation at the front of the house where no rain ever reaches. We're going to put in a small retaining wall along the front of the house, ostensibly for a raised flower bed.

What would I need / need to do to put some sort of trickle watering system in this raised area? I'm thinking of something that would require low maintenance in the warm season (perhaps automatic) and material that can withstand frigid winter temperatures without breaking or malfunctioning. Coming out through the cellar wall is no problem.

Answer
it sounds like a drip irrigation system may work for you. you would need a backflow device of some type, a remote control valve, filter, pressure regulator, dripline, and a few misc parts... now, before it gets too complicated you may be able to use a kit that you could connect to a hose bib on the outside of your house. check this out (cut and paste it into your browser)  http://www.dripirrigation.com/drip_irrigation_info.php?cPath=22&products_id=33 I have never used this website but do recommend the brand "DIG." Let me know if you need any further help and to find out more options do a search on "drip irrigation kits." I think you will get all the instruction and installation manuals you need with the drip kits but feel free to contact me should you need any help.