Hi Travis, I did this for a while in my raised bed garden. Olla's are expensive so I found lots of those clay wine cooler things at GoodWill worked ok.

They need constant refilling which was just as large a burden as just watering with the hose. The biggest drawback I found was how much 'real estate' they took up in the bed. Plus, as you state, the roots gravitate to the water source. Not sure it would be good for your purposes. If you want to try it, I have a couple of the containers you can have. I'm near 43rd Ave and Peoria and can just leave them out front for you. LMK

Eventually I laid down a drip hose connected to a water tap that stayed turned on and set a timer for watering. That worked well. Harbor Freight has cheap drip hoses. This is a real simple, easy to use timer

I would not use that for transplanting reasons alone. I also thing that roots against a contantly wet surface could cause problems. If the ollas dried out the roots could die. https://www.youtube.com/watch?v=GRiLhrY2CMc

Steve

Thank you both for your comments. Your thoughts are in line with my concerns. I have my containers attached to a drip system so I'm not worried about the actual watering. I thought it would probably help cool the container. But, it takes up so much room and I imagine before too long the roots wrap it up and create a serious problem when it's time to repot. I think I'll stay away from it for now.

You could set the containers on top of the soil sunk in an inch. a ring of six small pot around the pot's periphery.

I think I'll get creative this summer with placement, as Steve suggested.