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Blog Post Photo Gallery - Is this even possible?

I have had my blog on WordPress for several years and there's always been one thing that I wanted to get working that I have never figured out.  I have been hearing great things about SquareSpace so I began my trial yesterday and have started importing my posts over from WP.  I was hoping that I'd finally be able to accomplish what I wasn't able to do in WP but now I'm seeing that I still can't do it.  My blog is just made up of events that my wife and I get in to.  Each post is composed of a bunch of pics and a narrative of what it was we did.  I want there to be a single pic at the top of the post and when you click on that pic, the gallery opens in Lightbox and you can then scroll nicely through it.  Although I have seen a bunch of posts on SS and WP forums from people trying to accomplish the same things, it does not appear that there has been an acceptable solution to this.  I currently use the NextGen Gallery plugin for WP on my blog but I'm not happy with the way it works.  I am wondering if there is perhaps a better way to accomplish what I'm trying to do or if I just need to give up.  I am more than willing to stay on WordPress if there is a good solution there.  I should also mention that I'm not a programmer/web developer.  

I appreciate any help that can be lent.
Thanks in advance.
-Chris
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gwkg
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I know it's not exactly what you are asking for, but this plugin lets you put your pics from Flickr into a slideshow

http://tylrslidr.com/

That slideshow could be at the top of your post, with the text underneath as you embed it with a shortcode.

Its not a lightbox, but I think from what you explained, a lightbox wouldn't be the best user experience.  With this style of slideshow they could read the post and see the pics at the same time.

Still, you would have to be ok with sharing your pics on Flick, too.

There is also flickrpress, which does use a lightbox.

http://wordpress.org/extend/plugins/flickrpress/

Trying to find a wordpress plugin to do exactly what you what it to do usually takes some customization as the plugin author usually creates a plugin to do what they want it to do.
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HarkinsIT

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Hmm.  That tylrslidr plugin does look interesting but I'd rather not have to throw all of my pics up on Flickr to use it. I do like the way it works though.  Might be a possibility if I decide to raise the white flag.

I understand what you're saying about plugin authors.  I have been looking for a way to accomplish this for over a year on and off and in my searches around the web, I always come across lots of other people trying to do the same thing and I'm always amazed that no one has made it happen yet.  I'd definitely be willing to pay for something, as I'm sure others would too.  Oh well, I guess the search continues....

Thanks for the info!
-Chris
It shouldn't be too hard for a freelancer to customize the code from that plugin to pull the images from a folder on your site instead of from Flickr.
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