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In our experience the keywords in the URL do play (but pales in comparison to other on page signals).  If you have multiple iterations of these sites, why not do some A/B testings to see what woks best.

Acknowledging what the previous posters are saying but if you are going to leverage this, do a little key word research and find out what the predicted searches look like.  We do find that order can make a difference, i.e.  Lake Tahoe Boat Rental vs Boat Rental Lake Tahoe.  Maybe play with the inverted order of the title tags as a contrast.

Again, other signals are much more important but all things being equal we have seen positive movements with keywords in the URL.

Because most will want to know before they answer but what was your redirect strategy from the previous platform?

Indeed.com uses the double hyphen in their URL scheme and it certainly doesn't seem to hurt them.  I Imagine this is due to being able to reconstitute this back from URL rewriting so they know the difference between a dash in the URL that replaces a "space" vs a -- which would reconstitute back to a dash.

Example:q-Tennis-Channel-jobs.html

Maps back to the company Tennis Channel

Example: /cmp/Sag--aftra

Maps back to the company Sag-Aftra