In case you want to have tooltips with two different show events I suggest to use two separate RadToolTipManagers, each of them with the desired show event set. After that you can tooltipify the elements according to the desired settings.
One possible solution is to use the built-in automatic tooltipifying as you intended - in order to tooltipify a specific area, you should wrap it in some wrapper (DIV, Panel, etc), set the desired manager's ToolTipZoneID to the ID of this wrapper and also set AutoToolTipify to true - an online demo about this is available below:
Another option is to populate each manager's TargetControls collection with the desired controls as shown in the following demo:
Please, choose the solution which best fits ypour needs and let us know how it goes.
the Telerik team