Retainer Venture Question

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What are the requirements to do Highland Exploration III? All my gathering jobs are at level 30....

Well, you have the answer right in the sceen, the number 30 is red (I had problems at first too, being colorblind), so that means that your retainer needs 30 gathering to be able to do that exploration.
Just equip some gathering armor and you will be fine.

It is referring to your gathering stat (look under attribute) you need at least 30 Gathering stat to do this.

Both retainers are maxed out at 25 for their assigned job. How do I break their cap?

30 isn't the level needed, it's the gathering needed. Gathering is an attribute that you can find on gear.

For instance, the Cotton Doublet Vest of Gathering has a gathering rating of 28.

For your actual situation, your retainer needs to meet the required gathering stat. Basically you need to give your retainer better gear.

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Originally Posted by gardei

Both retainers are maxed out at 25 for their assigned job. How do I break their cap?

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You need to actually level your own gathering classes before you can max out your retainer's Botanist, Miner or Fisher level. So if you ever want a level 50 Botanist Retainer, you need to have your own Botany level at 50.

Like Amnesia mentioned you need to raise your gathering stat.
As gathering isn't a stat that you gain naturally you will have to equip your retainer with gear that has this attribute.

The requirements on lower exploration ventures are not that high, so most of the time you can easily get the amount of gathering needed by equipping your retainer with both a main and off-hand tool close to their level.

As for the level cap, like Parawill mentions you will need level your own botanist first.

Gathering refers to the gathering stat, not you or your retainer's current level. Easily corrected by merely upgrading your retainer's armor. There's an option near the bottom of the list to view what they are currently wearing. Most the gear is available for purchase through vendors around your leveling areas, if it's not cheaper off the market board.