Then we add a rider, it's far cheaper to add a CR5 rider, instead of adding another CR to make it intelligent.

if we don't want to risk the rider being targeted, then we make an intelligent brain symbiote, we can use the creatures the Illithids used on those Ironborn children as a template, give such a creature intelligence, and let it command the Anaconda, if it grow tired of that, we just grow it a soul less body to inhabit.

We can even give the rider some spellcasting, having a few buffs would improve the Anaconda significantly.
That would be impractical and overly complicated. The less moving parts the better. A rider is superfluous.

There are plenty of sentient base creatures we can use, which become acceptably intelligent when the Advanced template is applied.
 
That would be impractical and overly complicated. The less moving parts the better. A rider is superfluous.

There are plenty of sentient base creatures we can use, which become acceptably intelligent when the Advanced template is applied.
Can you get it to Colossal from those creatures, without going above CR13? because I'm trying to keep the CR down.

Also I'm thinking we could use a tiny Viper for the rider, it's so small and the Anaconda so big, that it could literally hide in the Anaconda's ear canal during battle.
 
Even if we up the Anaconda's CR by 1 by making it intelligent, the monthly cost of hiring 1 Anaconda, 5 Sharks, and 1 Dolphin will still only be 4840IM, leaving the Whales with 2160IM a month for other expenses, so even with the Anaconda made more expensive they can afford it, we can still look for better of course, but if we can't find anything, I think the pod guardians we have assembled will work fine, we just have to find a good CR+1 intelligence granting template for the Anaconda.
 
Looked for intelligence granting templates, and I must say I'm still more inclined towards a commander, we can make the Anaconda a plantblood and have it in constant communication with a Cleric creature plantblood, that stays underoil, buffing healing and commanding the Anaconda, we can have 2-3 of these Plantblood commanders, they don't need to be higher than CR5, so they wont be all that expensive, and their healing and buffs will benefit the Anaconda a lot.
 
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