Convey <http://www.getconvey.com> may fit your needs.  It's a hosted web 
application which, when integrated in your app, figures out the right Help 
topics to show users based on their context.  Here's a screenshot:

<https://lh3.googleusercontent.com/-CkBSpjtyBB0/Ua6Jk8ltnqI/AAAAAAAAAAM/Bss3fPxVJTM/s1600/Screenshot+-+Sample+App+-+Settings.png>

It's super easy to install and it lets non-developers on your team update 
the Help.  The downsides are that it's not inline (though it is 
context-sensitive) and it's not free.

For full disclosure, I do have to mention that I'm the creator of Convey. 
 I also happen to think it's a great tool :)

On Friday, May 31, 2013 8:42:23 AM UTC-4, ppetree wrote:
>
> My reason for using ajax is three fold:
>
>    1. To do a real context sensitive help system would require more help 
>    text than would be feasible to integrate for each control, dictionary 
>    definition or decision point on each page. 
>    2. By including just the <div> we minimize the number of bytes 
>    transferred thereby reducing bandwidth requirements and improve page load 
>    times. Why transfer data on help points when those may never be accessed 
> or 
>    accessed only once? 
>    3. The help system could include short videos (we're using camstudio 
>    to capture desktop mouse moves and voice over).
>
>   
> On Thu, May 30, 2013 at 7:05 PM, Jason Westbrook 
> <jwest...@gmail.com<javascript:>
> > wrote:
>  
>
>> If you want to use tooltips or popovers you could use the PrototypeJS 
>> Twitter BootStrap tooltips or popovers
>>  
>> https://github.com/jwestbrook/bootstrap-prototype
>>  
>>  
>>  
>>  
>> Jason Westbrook | T: 313-799-3770 | jwest...@gmail.com <javascript:> 
>>  
>>  
>> On Thu, May 30, 2013 at 3:28 PM, Walter Lee Davis 
>> <wa...@wdstudio.com<javascript:>
>> > wrote:
>>  
>>
>>> I think you could make the whole thing pretty simply. Rather than 
>>> creating a separate handler (with each()) for each .help element, you could 
>>> wrap the entire thing in one "on" handler, which you would not need to 
>>> customize per page or worry about dom:loaded or anything:
>>>  
>>> document.on('click', '.help', function(evt, elm){
>>>   var tip = elm.down('div');
>>>   new Ajax.Updater(tip, 'path/to/help', {
>>>     parameters: {id: elm.id},
>>>     onCreate: function(){
>>>       tip.addClassName('loading');
>>>     },
>>>     onSuccess: function(){
>>>       tip.removeClassName('loading');
>>>       tip.addClassName('tooltip');
>>>     }
>>>   });
>>> });
>>>  
>>> document.on('click', '.tooltip', function(evt, elm){
>>>   evt.stop();
>>>   elm.update().removeClassName('tooltip');
>>> });
>>>  
>>> That's expecting a structure like this:
>>>  
>>> <div class="help" id="widget_1"><div></div></div>
>>>  
>>> You could use some other construction if you like, but that would do the 
>>> trick. The rest will be creating the CSS for the tooltip, and the Web 
>>> service to fill it in.
>>>  
>>> If you didn't want to get the Ajax thing going, you could also just put 
>>> the tooltip in the help element itself, maybe in a data-attribute. That 
>>> depends on how much content there would be. It would be completely 
>>> instantaneous.
>>>   
>>> Walter
>>>  
>>>  
>>> On May 30, 2013, at 2:24 PM, Phil Petree wrote:
>>>  
>>> > I'll play around with it on Sunday and see what I can cobble 
>>> together... of course it looks like you did most of the work in 5 minutes 
>>> and I'll spend most of the day playing around with it! LOL
>>>  
>>>  
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>>>  
>>>  
>>>
>>  
>>
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>  
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