I did exactly this two weeks ago, only with my mid-2012 13" MBP, which also has TB1 (and USB 3.0 ports). Monitor is a Dell U2717D plugged into the DisplayPort on the Caldigit TS3 Plus.
It works perfectly for me except for one small, laptop-specific issue; if I unplug and re-plug the TB1 cable multiple times (if I'm working from home and take the laptop away to sit on the couch, then come back and plug in at the desktop for a while, then an hour later back to the couch, then back to the desktop, etc etc), after somewhere between three and six unpluggings/repluggings my external monitor (Dell U2717D) doesn't come back on when I replug. I don't know if it's a monitor, hub or (elderly) laptop issue, but whatever it is, a quick reboot fixes the problem. It's not really causing me any serious issues - maybe once a week I have to do an extra reboot.
All that said, as you have an iMac I'm sure this wouldn't apply to your use case - I'm assuming you're not moving your iMac three times day while still booted!
Incidentally, I also have an OWC ThunderBay4 TB2 hard drive enclosure, which is daisy-chained from the dock's TB3 pass through port, using an Apple TB2/TB3 adaptor -> Apple TB2 cable. It work flawlessly, achieving max data throughput speeds from the 3.5" HDDs therein. I'm glad I paid for the Apple cables - it all just works.