One thing you’ll want to do if you have any chance at all is stun Yoshimoto’s Pineco. Deep Breath and its hefty defenses make it a royal pain for even a Fire-type to burn out, especially if it gets the chance to Bug Bite and nick a potion from you. Making it flinch for just one turn can give you a chance to take it out without the thing ever recovering its HP, drastically reducing the difficulty and length of the battle.
As an alternative, you can damage it enough to make Yoshimoto use Deep Breath, and then stay clear of it for a while- while equally viable, this strategy is a lot harder to use, especially with the Pokemari balls constantly adding clutter and threat to the field- so while possible it’s not an option you should try to rely on.
Securing Chrysalia takes a bit of doing- even if you conquer the concepts and strategies, it takes a lot of movement and attacks to finish off the opposed forces. It shouldn’t be too hard to recruit everyone but Yoshimoto from here- but don’t worry overmuch if you don’t succeed at that. Not only do the Warriors here repeatedly show up in ‘wild encounters’, but Yoshimoto himself does as well from time to time... sadly, he’s just as enduringly irritating to face off with as in this battle.
With the fight complete, Yoshimoto laments that the battle- and the fun- are over. The dull Warlord takes a prodding from Sessai and a bit of time to realize that this means he is no longer Chrysalia’s Warlord, which finally gets him a bit flustered. Well, a lot flustered. After you distribute any new army members to other fortresses if necessary, you’re given a chance to save, finally done with your fifth conquest.
At this point you should go ahead and finish out the month. If you brought a large army to Chrysalia, you probably don’t have any chance to bring anything in there yet, which really isn’t a big deal. With each new conquest from this point, you’re generally going to be doing a severe reorganization of forces- after all, each fortress specializes in a different Pokemon type, and that means bringing a different attacking troop. That also means that each time you capture a new area, where you want all of your Warriors changes also. For instance, once all your Warriors with Grass affinity have their best possible partner, there’s little to no reason to host troops in Greenleaf, as the only way to reach there is from other territories you control.
At the same time, Warriors with Fire Pokemon can, for instance, be stationed in Chrysalia- where they’re just as effective at handling the locals as they would be in Greenleaf, and are also much closer to the front of battle if you need to swap them into your attacking troops.
This makes keeping track of your fortresses very important- even if they’re being managed by other Warriors in your army. You need to know what your resources are and where to go to improve them at all times, even if you always use the same attacking group- there’s only so much time you have in real-life terms to spend overpowering the same five or six Pokemon so they can take on anything, regardless of weaknesses and resistances.
Anyway, with the month complete, it’s time to move on.