CRJ-700 First Officer reported multiple caution message resulted in expeditious handling to divert airfield. First Officer also reported Captain inexperience of aircraft and leadership substantially increased workload.

Narrative

On takeoff and climbout we received a GLD UNSAFE caution message. We ran the QRH at a safe altitude in the climb and it indicated a 40% increase in landing distance for the expected wet runway. Dispatch was notified and we elected to continue since we were still within available landing distance. On final approach we received an A/SKID OUTBD caution message and had to break off the approach. QRH determined an additional 85% increase in landing distance on a wet runway. In total we needed more than 12;000 ft of runway. Neither the destination nor our alternate would have been feasible. Our fuel situation indicated ZZZ was the only option with a 10;000 ft or 11;000 ft runway. We [requested priority handling] and diverted to ZZZ. Landing was uneventful with a longer rollout.Cause: Mechanical issue was the primary contributing factor. A/SKID OUTBD caution had appeared on the previous flight and was addressed by Maintenance prior to our departure. I was flying with a brand new ERJ-CRJ transition upgrade Captain on his first trip after IOE. His inexperience in the aircraft and in leadership substantially increased my workload as pilot monitoring all the while dealing with caution messages. Multiple times I had to point out corrections to the flight path and energy state of the aircraft. I also had to prompt the Captain to run our CRM models every time a caution message appeared.Suggestions: Additional contingency fuel in this situation would have been helpful in preparing for the diversion and dealing with the caution messages.