I already answered your support ticket and for your convenience and for others who might have the same question I pasted it below:
Your tooltipifying code seems to be correct and I am not sure what is causing the issue and I will need to examine a sample demo which shows your exact setup and configuration. However, before you take time and effort to prepare and send such, I would like to inform you that after we make this setup work, it will not work as you expect and the first tooltip will hide once the second one shows. This is due to the fact that only a single tooltip might be visible at any given time. This behavior is by design and will not be changed as changing it would defy the purpose of the control.
The purpose of a tooltip is to provide additional information for a given element. It is not meant to be used as a popup control or as a draggable panel. For this purpose we provide RadWindow and RadDock controls. Both of these controls allow more than one visible element of the kind on the page.
Our suggestion is to consider using RadWindow and RadDock controls.
Please, let us know how you decide to proceed and send us a sample demo if needed along with detailed explanation and instructions and we will do our best to help.
the Telerik team