Hi Chaz, I had a similar problem on my website which is now fixed and may help you, might not though.
I had a static home page and a blog page set up under Appearance – Settings – Reading.
On the blog page I set the template to be a blog template and the layout to be right sidebar.
I couldn’t for the life of me get the main blog page to show the sidebar, even though the actual post pages showed the sidebar.
I was advised to de-select the blog page under Appearance – Settings – Reading, ie so there’s no blog page selected. My main blog page then displays with a side bar.
It’s a bit strange but worked for me. Hope it works for you too.
Jules