I'm unfamiliar with the specific mechanics of Bootstrap (kids, my lawn, get off), but looking at this from a pure javascript/dom point of view it appears your hover is over the following div
<div id="hardware-overlay" class="img-circle" data-placement="top" data-content="The arduino-compatible hardware connects
five environmental sensors to the internet Wirelessly." data-original-title="" title="" style="">
</div>
When you roll-off/mouseout of of the popover, the above div's DOM node is changed to include a style="display:none;"
<div id="hardware-overlay" class="img-circle" data-placement="top" data-content="The arduino-compatible hardware connects
five environmental sensors to the internet Wirelessly." data-original-title="" title="" style="display: none; ">
</div>
Because this div is not being displayed, there's nothing to trigger the pop over. If I run the following javascript from Chrome's debugger console
jQuery('#hardware-overlay').css('display','block')
I can get the rollover to run again (with the same "only runs once" behavior)
Hope that helps narrow down the problem.