Permalink Structure Change and Redirect Questions

I have blog pages have been set up to include the date in the url.
Ex: clientname / 2014 / 09 / dwi-lawyers-mn-choose /
Am I correct in assuming that Google is looking at this page as being at a click depth of 3? (And therefore being a page that Google is less likely to crawl)

My larger issue is if I should change the permalink structure to not include the date in the URL. I mean, I don't want the date in the URL, but I'm wondering about the work it would take to manually redirect 300 pages, and all the other issues that could arise. Like if I change the Permalink structure, what happens to all the existing pages? Also, losing rank isn't really an issue because the traffic is super low anyway.

I would use Yoast Premium, but the client doesn't want to pay for it.

Any clarification would be much appreciated! Thanks!