What voltage does your alternator produce? That's the starting point. From there you can determine if its reasonable to get charging to your trailer. For example, if your alt produces 13.9V nominal, its not going to charge well, even if the battery is right next to the alternator. Add a few tenths of a volt drop in the wiring, and charging is going to be anemic at best.
If your alternator is outputting 14.5V, then you have a good chance. If you can get 14.1-14.2V at the battery, you will have decent charge rates. So lets assume you can tolerate a 0.4V drop in this scenario. That is 0.2/14.5=2.75%. Choose a reasonable current, say, 20A, and find the wiring that results in less than 2.75% drop. Remember that connections and fuses will add some to the voltage drop.
The DC-DC chargers are more flexible. Look at their specs. Whats the minimum input voltage? If its say 12.5V (with an external ignition trigger/control), then you are at 2/14.5 = 13.75% drop allowed.
In addition, because the DC-DC boosts the voltage, if your alternator is on the low end voltage wise, the DC-DC will allow higher charge rates than normally possible, even with a long wire run.