Last winter I tried a similar method, only to find that peach web of mold on everything in less than a week- of course all with their lives sucked out of them by the gnats and mold. This method works for older plants, my blueberries do excellent, but my figs don't like to have soggy feet. I found that what really work is to put about an inch of broken down wood chips at the bottom, the chips soak up the water and work as a sponge, but any excess, flows out.
Once a week I sit the pots in a bucket with water, the chips soak up, and once out of the bucket all excess water runs out. So far, so good, how challenge is to stay alive for the winter. Hope you have a better less moldy city for the cuttings.