assuming your power source has no protection, then your 300-1000 ft pull would be service. As RB1 states Art 230 says you must have overcurrent protection on the service condutors (230.91), so they would terminate in a breaker or fused disconnect. That disconnect could aslo be your transformer protecton, size per 450.3 Look at 240.2(F) to determine the need for overcurrent protection for the conductors on the secondary side of your transformer. If you are going to a three wire (240/120) secondary, you will need overcurrent potection on that.
In your second scenerio,again 230.91 & 450.3 will require overcurrent protection ahead of your step-up transformer. As this is a could be a two-wire primary/secondary, you might get by without secondary OCP, but your end location will, by nEC, probanluy be classified as a structure and you will need OCP there to protect the feeder. The secondary of that step down transformer will agin need OCP if it's a 3 wire secondary.
For the most part, it sounds like you will need breakers or fuses on the line and load side of your transformers when you take 450, 230, amd 240 into consideration..