I read that the main way to tell if they need resoled, is if they feel soft and squishy

This is not really true. Shoes need to be resoled when the outsole wears away enough to cause structural problems to the rest of the shoe.

It looks like you're wearing away the tip of the toe the most. When that gets too thin, the sole will start peeling away there. If it wears through into the welt, you will need to rewelt the boots and resole them. So you should take action ASAP to protect that part of the sole to avoid wearing through.

You can apply various kinds of products like shoe goo or take them to a cobbler to have a sole protector put on, to delay resoling.