It may just be an issue with the first three gangs you can take territory from in the new system, but it seems like the opposition's Merchant rating is always 1. "Buy Them Off", the slot that challenges merchant skill, just flies by. It takes maybe ten seconds to carve out a new chunk of the micronation.
Viewing post in Update 0.36.3 - Mission bugs comments
There's a bit of randomness involved in the opponent's skills, but after the Meat Heads (first opponent) it shouldn't be possible for skills to hit 1 anymore as of 0.36.3, and if it is then there's probably a bug. I'll dig a bit deeper and make sure everything is working as expected.
EDIT: The changes that make that impossible are in the current build, not 0.36.3 so it's fully possible for the first two enemies to spawn with 1 in a skill and the 3rd could spawn with 2. I'll still be investigating, just in case something was miswired.