I’m unclear what is happening here. The link you started the thread with does appear to have the right tags. However, it is one of the “attachment” pages on your Wordpress site, and has a strange URL as a result.
I just tried another one of your posts http://tall.life/an-old-house-for-tall-people/ and posted the link directly into a Tweet - a card appears to show fine.
So my suspicion here is that this is to do with attachments/standalone images, vs full posts.