Pictures/Videos Don’t Wrap Correctly Within Template

Hi,
Not sure how to describe this, and I am no coder. I have a friend who’s helping me with the CSS but she’s not an advanced WordPress user either.

Please see https://www.ispithotfire.com/ for reference.

Also: https://www.ispithotfire.com/2007/12/13/and-even-more-shopping/
and https://www.ispithotfire.com/2008/01/12/photo-highlights-from-the-usa-trip-2-weeks-part-1/

1) I would like it so that my site automatically senses that there are too many pictures in it and wraps within that left “frame”. Basically I feel like the site should know when things are about to get messy and go down a line when it needs too. Maybe (if there’s only one object on the line) if the photo or video is simply too big, it resizes that image to make it fit in the frame, not sure if that’s too much to ask, but I definitely would think it could sense if there’s multiple photos or videos, it could “wrap” automatically instead of creating the mess you see in the links.

Also, even if I manually press place <br> if I sense there are too many photos, I cannot manually get a new line to go down- no matter what, I seem stuck with the mess.

2) I have a kind of footer for each blog post, where you can share the post or see related posts. For some reason, the blog will wrap it around a photo or video if there is one on the blog post, but I feel like it should act like it does around text- also the distinct bottom of the post, separated from the content of the entry.

See https://www.ispithotfire.com/2007/12/25/brrrr-its-cold/ for what it should look like.

Thanks for any ideas for help!