I’m testing various and sundry methods of setting up multiple photos within my posts that allow for clicks on my photos to take the clicker to my photography website, gallery, and (ahem) storefront. One of the blogs I follow: Travel Photography by Dmitrii Lezine, commented that he uses Windows Live Writer, which links to his WordPress blog, and he can upload multiple photos rather than one per post. So I thought I would give it a whirl.
Ok, let’s see how this works…..By golly, it works!
What you do, once you set up Windows Live Writer, is link it to your blogsite, so that any post you type on Live Writer gets sent to your WordPress site, with all your regular WordPress theme, widgets, etc. To insert the photos, you click on Live Writer’s picture icon. There are several ways to insert a photo. I tried to insert it via web/Smugmug directly, and I couldn’t get that to work (dunno why). So, I went into SmugMug and clicked on the photo I wanted to insert, and copied that photo’s URL. I then went back to Live Writer and inserted that same photo from my computer, right clicked, and hyperlinked the photo to my SmugMug gallery using the URL I previously copied from the photo in SmugMug. After publishing this post, I clicked on each photo and voila! Each time I was taken to my photo website (via SmugMug) where the XLarge size of that particular photo was displayed. I could close out of that photo and I could see all the other photos in that particular gallery.
Thanks, Dmitrii!
Where The Trails Take You Photography 
I’m glad it worked for you! You can preset some settings for your photos in Live Writer as well, so the next time you insert the photo, they will have all of those default settings – like size, captions, watermarks etc. Saves time. Also, if you want to get rid of the shadow on your photos, just use one of the pciture controls to display it flat without any special effects.