The basic design of the sub-irrigated (self-watering) bucket planter shown in this cutaway diagram is sound but it has a potentially fatal flaw (or two).
Note the red funnel at the bottom used to create a soil wick. Unfortunately, it will become a “choke point” over time as the roots grow down into the neck of the funnel. I also don't see any indication of an overflow drain hole to prevent flooding the planter in a rain storm.
A much better idea is to use a plastic container such as a plastic drink cup or yogurt container to create the soil wick. See this post about root growth in recycled pop bottle planters.
The Greenroof Growers blog has an excellent tutorial on making sub-irrigated bucket planters. The blog is written by experienced growers using sub-irrigation planters on Chicago area rooftops. I would highly recommend reading and following their instructions.






