On one freeranger is a great frame for the sort of local mix and match riding you describe. Loads of clearance. I’ve had 45mm with full guard on mine.
I upgraded to a Specialised Crux over the summer. Massive clearance again. Runs 47mm no problem. I absolutely love this bike for winter road, BWs, canals and cross racing.
Never tried the Checkpoint. Mate had one and likes it but I didn’t bother as I wanted more clearance