Blue23Rose, I have found that using a deeper pot, and as large as possible for the rebar post they are on, helps keep enough soil in the pots so that my plants make it through the extreme weather periods of July and August.
Your tipsy looks great!
One summer I had a sprained knee and knew I was not going to be able to keep the tipsy watered so I planted some hearty succulents in it. They did very well despite the periods of no water and are still growing there. No blooms except in early spring but they stay green with a bit of trailing greenery.