Karen,
I was thinking of you the other day, we (mother and I) went
plant hunting and I saw a big stack of half wine barrels, I read the directions on it that said about draining the barrel and having to cut holes in it.
Actually what Bill said is what I was thinking. (I have a wishing well I
plant in) I do those stupid packing peanuts in a 13 gallon garbage bag. poke holes in the bottom, peanuts, and a sheet of landscaping fabric (that lets through the water, NOT Plastic.) Throw dirt on top that and
plant.
I do the bag because I don't want the dirt on the wood of the wishing well, but it stays dry because of the top on it...)
But the idea of the hose on the bottom may very well work (something along the lines of the rain barrel collecting systems they have......
hoses out the bottom of the barrel...
Maybe inconspicuous..
You could put a regular pot or two in front of the hose to hide it..
I'm very interested in your final outcome.

Weezie
P.S. What about jasmine? Scarlet Runner Bean?
Cardinal
flower? Have you looked any up?