Rohann, test as you are going to compete/hunt. Do your initial load development with as cool a barrel as possible. You don't want heat issues to cloud your results.
Once you have a decent load or two, shoot them at the distance and conditions the rifle will be applied.
For hunting, I test from a cold barrel as close to the temp I will be hunting in. No use testing a 30C "cold" barrel when I am hunting near freezing. I want to know where that first bullet lands at any range I am likely to hunt at.
I will also test two follow up shots and see if there is any significant change in POI. If there is, I either have to live with it or get another barrel/rifle.
For competition, work your load/rifle under match conditions. For F class, I worked up my loads using low rd counts so nothing overheats and I am sure of the results - no shooter fatigue.
Then I test each load with several 20 to 25rds groups at distance in 15min or less to simulate match conditions. Obviously, testing is done in the warmer months. Hopefully, the last few shot are as accurate as the first.
Track how that barrel behaves as it heats up an fouls. Many factory barrels will 'walk' as they heat and also loose consistency (dispersion increases). Sometimes, this is greater then acceptable and a new pipe/rifle is warranted.
Quality BR barrels tend to be more stable even when scalding hot. Only testing will determine this.
Also, test the ammo. Many powders are affected by ambient temp so if you use that ammo in the cold, test in the cold.
For F class, my chambers are going to get very warm. As a final test, I will chamber rds and let them heat soak for a few minutes. I need to know that if I hold off shooting and leave a rd in the hot pipe, it will not cook off/overpressure or fly into the 8 ring.
For hunting, I might get the ammo damp and see if that affects anything.
You need to trust that rifle will perform if you do. Wasting time second guessing yourself or the rifle ensures you will not have the confidence to score.
It doesn't matter if this means groups are bigger then a dime. I will take consistency and predictability over a fussy bug hole shooter anyday.
Now the really hard part, practising and improving enough so you are as good as your rifle.
Jerry