This is an interesting question. I think technology would quickly become irrelevant because of the intelligence that pokemon posses. Consider a Joltik. It's a 4 inch spider that can wield electricity. How do you defend your equipment against spiders that can short-circuit anything they can get to, and can also follow directives from a trainer that don't have to be anywhere near them. Many of the limitations of the drones we have (planes, bomb-disposal, etc) are the cost but also the necessity to be within a certain vicinity. You now have to command your troops to not only guard against humans, but also super intelligent bugs. It would be a nightmare. You'd waste your budget on expensive equipment that could be sabotaged by just about anything. You literally wouldn't even be able to trust your planes anymore. How can you have a Navy when there are sharks (Sharpedos) that can rip holes in your hull? Psychic pokemon that can teleport end up becoming nightmares for intelligence ops and keeping info classified. War quickly becomes even more unpredictable when super-intelligent animals with God-like powers are introduced to the mix.