As "JR" said, "There's always a good amount of cold break regardless of using bags." How much trub you allow to transfer to your fermenter may be an individual preference. I primarily use a Fastferment and the less trub I transfer the less opportunity there is for plugs in the conical above the trub collection ball - less emptying the ball. So a good whirpool and 20 minute settle allows me to transfer more wort and less trub.
If you plan to use a ferment bucket, as said, the trub will not harm your beer... Hop bag and a screen on your pick up tube (as "JerB" suggested) and you're golden! I second "JR" about cleaning sooner than later. Rack out then immediately fill it with water and I bet that will help eliminate "crud" taking up residence in there.
After looking at your pictures again... is that small fitting in the bottom left corner for the temp probe? If so I'm wondering how that will work being that close to the bottom... If you are doing a PID controled recirculating mash, a lot of us put the temp probe in the recirc line either right out of the pump or where it goes through the sidewall/lid. Seems to work quite well.
Go for it! Happy brewing!
Don
Primary #1 - Joe IPA clone
Primary #2 - APA
Kegged - nothing :-(
Bottled - Oatmeal Stout, APA, Rye IPA